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Palladium Catalysis: Dependence of the Efficiency of C-C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)-C(sp2), C(sp2)-C(sp3) and C(sp3)-C(sp3) Bonds

ADVANCED SYNTHESIS & CATALYSIS (2023)

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Summary: A palladium-catalyzed strategy for constructing isoindole N-oxide ring by C-H functionalization of aldonitrones is presented. The protocol is versatile and allows for the introduction of various functional groups, even in sterically congested products. Transformations into spirocyclic isoindolines, isoindoles, and polycyclic isoquinolinium salt have also been demonstrated. Mechanistic studies suggest a Heck-type addition to the double C=N bond as the catalytic process.

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Palladium-Catalyzed C(sp2)-H Arylation of Peptides Directed by Aspartic Acid

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Summary: Here, we present a palladium-catalyzed C(sp2)-H diarylation or monoarylation of short peptides with N-terminal benzamide groups, using aspartic acid (Asp) as an internal directing group. This strategy offers several advantages, including a wide substrate scope, selective diarylation of peptides, and gram-scale synthesis. Moreover, this approach can be effectively applied for the synthesis of peptide-peptide conjugates.

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Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification

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Summary: A Pd(II)-catalyzed dehydrogenative remote C4-H coupling of indoles with unfunctionalized arenes at room temperature was achieved using a weak chelating trifluoroacetyl group as a directing group. Various substituents on the arenes were compatible with the dehydrogenative cross coupling reaction.

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Dual-Ligand Catalyst for the Nondirected C-H Olefination of Heteroarenes

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Palladium-Catalyzed Direct (Het)arylation Reactions of Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole and 4,8-Dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)

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Summary: This study investigated the palladium-catalyzed direct (het)arylation reactions of electron-withdrawing tricyclic benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative. Selective formation of mono- and bis-aryl derivatives was achieved under specific conditions. The direct C-H arylation of benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) with bromo(iodo)arenes and -thiophenes in the presence of palladium acetate and di-tert-butyl(methyl)phosphonium tetrafluoroborate salt proved to be a powerful tool for selective formation of 4-mono- and 4,8-di(het)arylated benzo-bis-thiadiazoles. Oxidative double C-H hetarylation of benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) with thiophenes in the presence of Pd(OAc)(2) and silver (I) oxide in DMSO successfully prepared bis-thienylbenzo-bis-thiadiazoles with moderate yields.

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Synthesis of 5,6-Dihydrophenanthridines via Palladium-Catalyzed Intramolecular Dehydrogenative Coupling of Two Aryl C-H Bonds

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Palladium-Catalyzed [3+2] Annulation of Aromatic Amides with Maleimides through Dual C-H Activation

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Summary: A palladium-catalyzed [3 + 2] annulation of substituted aromatic amides with maleimides is described, providing tricyclic heterocyclic molecules in good to moderate yields through weak carbonyl chelation. The reaction proceeds via a dual C-H bond activation, first selectively at the benzylic position and then at the meta position, resulting in a five-membered cyclic ring. The use of external ligand Ac-Gly-OH is crucial for the success of this protocol. A plausible reaction mechanism has been proposed for the [3 + 2] annulation reaction.

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Highly Stereoselective Synthesis of Bis-C-ferrocenyl Glycosides via Palladium-Catalyzed Directed C-H Glycosylation

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Palladium-Catalyzed ortho-C-H Alkoxycarbonylation of Aromatic Aldehydes via a Transient Directing Group Strategy

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Palladium/Silver Cocatalyzed Divergent Dimerization of 2H-Azirines for Regioselective Synthesis of Tetrasubstituted Pyrroles and Pyrimidines

Yongxing Zhao et al.

Summary: Unprecedented dimerizations of 2H-azirines have been achieved through the catalysis of palladium and silver. By altering the reaction conditions, fully aryl-substituted pyrrole and pyrimidine derivatives were obtained with moderate yields and regiospecificity. Control experiments demonstrated distinct catalytic effects of the two transition metals, and the proposed catalytic cycles provided plausible explanations for the chemodivergence and regioselectivity.

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Pd(II) and Rh(I) Catalytic Precursors for Arene Alkenylation: Comparative Evaluation of Reactivity and Mechanism Based on Experimental and Computational Studies

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Palladium-Catalyzed Tandem Diolefination Reaction of Benzaldehyde Enabled by a Remote Directing Group

Yangyang Wang et al.

Summary: A tandem diolefination reaction of benzaldehyde has been developed via Pd-catalyzed β-C(sp(2))-H olefination of the benzene ring and tandem C(sp(2))-H olefinationof acrylate. Remote directing group 2-((Aminooxy)methyl)benzonitrile was used in conjunction with the benzaldehyde substrate for C-H bond activation. Control experiments demonstrated the essential role of a remote cyano group in this novel diolefination reaction.

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Theoretical Investigations of Palladium-Catalyzed [3+2] Annulation via Benzylic and meta C-H Bond Activation

Rie Yoshimoto et al.

Summary: The reaction between aromatic amides and maleimides, catalyzed by palladium, leads to the formation of a product with double C-H bond activation, occurring at both the benzylic and meta positions. Computational chemistry studies reveal a stepwise mechanism involving a six-membered palladacycle, maleimide insertion, protonation of the Pd-N bond, and activation of the meta C-H bond. The site selectivity is determined by the interaction energy controlling the insertion of maleimide into the Pd-C(sp(3)) bond. The meta C-H bond activation step is identified as the rate-determining step based on the energetic span model. The 2-thiomethylphenyl group is found to function effectively as a directing group due to strong Pd-S bonding and the destabilizing effect of the deformation energy.

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PdII-Catalyzed Site-selectiveβ- andγ-C(sp3)-H Arylation of PrimaryAldehydes Controlled by Transient Directing Groups

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Summary: Pd(II)-catalyzed site-selective beta- and gamma-C(sp3)-H arylation of primary aldehydes is achieved by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are crucial for the observed reactivity. By minimizing the loading of acid additives, the ligand effect is enhanced to achieve high reactivities of the challenging primary aldehyde substrates. Site selectivity can be switched by changing the bite angle of TDG to match the desired palladacycle size, as supported by experimental and computational investigations.

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Direct Evidence for Competitive C-H Activation by a Well-Defined Silver XPhos Complex in Palladium-Catalyzed C-H Functionalization

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Summary: Increasing evidence suggests that silver salts can play a significant role in the C-H activation step of palladium-catalyzed C-H functionalization. In this study, a silver(I) complex was isolated through C-H bond activation and demonstrated its catalytic competence for C-H functionalization. It was found that silver carbonate, in the presence of a bulky phosphine called XPhos, can react with pentafluorobenzene to form the C-H bond activation product Ag(C6F5)(XPhos). The research also showed that silver complexes, along with palladium complexes, can achieve C-H functionalization even at ambient temperature. Moreover, the phosphine can be recycled through exchange between silver complexes, ensuring its continued use despite the consumption of silver carbonate during catalytic cross-coupling.

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Observing the Agostic Hydrogen in Pd(II)-Catalyzed Aromatic C-H Activation

Kaiwen Li et al.

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PdII-Catalyzed ?-C(sp3)-H (Hetero)arylation of Ketones Enabled by Transient Directing Groups

Yi-Hao Li et al.

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Ligand-Enabled C-H Hydroxylation with Aqueous H2O2 at Room Temperature

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The Real Structure of Pd(OAc)2 in Various Solvents

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Palladium-Catalyzed Site-Selective [3+2] Annulation via Benzylic and meta C-H Bond Activation

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Summary: The palladium-catalyzed [3+2] annulation of aromatic amides with maleimides via the activation of ortho benzylic C-H and meta C-H bonds is reported, with a key role played by the presence of a 2-methylthiophenyl directing group for the success of the reaction. The irreversible cleavage of these C-H bonds leads to the formation of five-membered cyclic products.

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C-H Activation and Cross-Coupling of Acyclic Aldonitrone

Jakub Brzeskiewicz et al.

Summary: The palladium-catalyzed activation of C(sp(2))-H bond in an easily E,Z-isomerizable aldonitrone with an ester group at the C terminus enabled its cross-coupling with various aryl and heteroaryl bromides to produce ketonitrones. The reactions exhibited high E selectivity and the use of sterically hindered carboxylic acid as an additive, along with a non-polar solvent like toluene, was crucial for achieving good yields of the cross-coupling products. The obtained ketonitrones were further shown to be useful in dipolar cycloaddition or nucleophilic addition reactions.

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Pd-catalyzed Intermolecular Dehydrogenative Heck Reactions of Six-membered Heteroarenes

Jean Le Bras et al.

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Pd(II)-Catalyzed Fujiwara-Moritani Reactions for the Synthesis and Functionalization of Substituted Coumarins

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Transient Directing Groups in Metal-Organic Cooperative Catalysis

Clement Jacob et al.

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Marco Lessi et al.

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Palladium(II) Complexes of N-Heterocyclic Carbene Amidates Derived from Chalcogenated Acetamide-Functionalized 1H-Benzimidazolium Salts: Recyclable Catalyst for Regioselective Arylation of Imidazoles under Aerobic Conditions

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Buttressing Salicylaldehydes: A Multipurpose Directing Group for C(sp3)-H Bond Activation

Akira Yada et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Site-selective C-H arylation of primary aliphatic amines enabled by a catalytic transient directing group

Yongbing Liu et al.

NATURE CHEMISTRY (2017)

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Role of Silver Salts in Palladium-Catalyzed Arene and Heteroarene C-H Functionalization Reactions

Monica D. Lotz et al.

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Synthesis of 3-(2-Olefinbenzyl)-4H-chromen-4-one through Cyclobenzylation and Catalytic C-H Bond Functionalization Using Palladium(II)

Yu-Feng Lin et al.

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Key Role of PdIV Intermediates in Promoting PdII-Catalyzed Dehydrogenative Homocoupling of Two Arenes: A DFT Study

Lei Zhang et al.

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Palladium-Catalyzed C-H Activation: Mass Spectrometric Approach to Reaction Kinetics in Solution

Jiri Vana et al.

ORGANOMETALLICS (2017)

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Ligand-Promoted Direct C-H Arylation of Simple Arenes: Evidence for a Cooperative Bimetallic Mechanism

Jaewoon Kim et al.

ACS CATALYSIS (2017)

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Ligand-controlled Regiodivergent C-H Alkenylation of Pyrazoles and its Application to the Synthesis of Indazoles

Hyun Tae Kim et al.

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The role of trinuclear species in a palladium acetate/trifluoroacetic acid catalytic system

Jiri Vana et al.

DALTON TRANSACTIONS (2017)

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A Direct Arylation-Cyclisation Reaction for the Construction of Medium-Sized Rings

Daniel Whitaker et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Ring Construction by Palladium(0)-Catalyzed C(sp3)-H Activation

Olivier Baudoin

ACCOUNTS OF CHEMICAL RESEARCH (2017)

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C-H-Activated Direct Arylation of Strong Benzothiadiazole and Quinoxaline-Based Electron Acceptors

Junxiang Zhang et al.

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Palladium-Catalyzed Selective C-H Activation: A Simple Method to Synthesize C-3 Site Arylated Quinoline Derivatives

Yongqin He et al.

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Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)-H Alkenylation and Application to Alkaloid Synthesis

Philipp M. Holstein et al.

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Catalytic C(sp3)-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ

Yan Xu et al.

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Synthesis of Benzobis- and Benzotrisbenzofurans by Palladium-Catalyzed Multiple Intramolecular C-H/C-H Coupling

Hiroyuki Kaida et al.

CHEMISTRY LETTERS (2016)

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Easy Access to Difluoromethylene-Containing Arene Analogues through Palladium-Catalysed C-H Olefination

Changdong Shao et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

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Palladium-catalyzed site-selective C-H alkenylation of imidazo[2,1-b]thiazoles

Guoli Huang et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2016)

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Ag(I)-Catalyzed C-H Activation: The Role of the Ag(I) Salt in Pd/Ag-Mediated C-H Arylation of Electron-Deficient Arenes

Daniel Whitaker et al.

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Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds by Silver-Mediated C-H Activation: A Synthetic and Mechanistic Investigation

Sarah Yunmi Lee et al.

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Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

Ke Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group

Yongwei Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants

Shuya Yamada et al.

ORGANIC LETTERS (2016)

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Unraveling innate substrate control in site-selective palladium-catalyzed C-H heterocycle functionalization

Hwanho Choi et al.

CHEMICAL SCIENCE (2016)

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Factors Controlling Stability and Reactivity of Dimeric Pd(II) Complexes in C-H Functionalization Catalysis

Brandon E. Haines et al.

ACS CATALYSIS (2016)

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Two Consecutive Palladium(II)-Promoted C-H Alkenylation Reactions for the Synthesis of 3-Alkenylquinolones

Veronica Ortiz-de-Elgue et al.

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Chiral γ-Lactams by Enantioselective Palladium(0)-Catalyzed Cyclopropane Functionalizations

Julia Pedroni et al.

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Synthesis of Thieno[3,2-b]benzofurans by Palladium-catalyzed Intramolecular C-H/C-H Coupling

Hiroyuki Kaida et al.

CHEMISTRY LETTERS (2015)

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Pd(II)-catalyzed Chelation-assisted Cross Dehydrogenative Coupling between Unactivated C(sp3)-H Bonds in Aliphatic Amides and Benzylic C-H Bonds in Toluene Derivatives

Teruhiko Kubo et al.

CHEMISTRY LETTERS (2015)

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Divergent Synthesis of Aeruginosins Based on a C(sp3)H Activation Strategy

David Dailler et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

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Palladium-Catalyzed Construction of Heteroatom-Containing π-Conjugated Systems by Intramolecular Oxidative C-H/C-H Coupling Reaction

Kenta Saito et al.

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Palladium-Catalyzed [3+3] Annulation between Diarylamines and ,-Unsaturated Acids through CH Activation: Direct Access to 4-Substituted 2-Quinolinones

Rajesh Kancherla et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

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Palladium-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Benzofurans with Uracils at Room Temperature

Ebrahim Kianmehr et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery

Jessica A. Hall et al.

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Palladium-catalysed oxidative cross-esterification between two alcohols

Jianhui Xia et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

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Pd-catalyzed oxidative C-H alkenylation for synthesizing arylvinyltriazole nucleosides

Jingjie Tang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

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Palladium(II)-Catalyzed Direct C-H Alkenylation of Thienothiophene and Related Fused Heteroarenes

Tomohiro Morita et al.

ORGANIC LETTERS (2015)

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Alkenylation of Phosphacoumarins via Aerobic Oxidative Heck Reactions and Their Synthetic Application to Fluorescent Benzophosphacoumarins

Cheol-Eui Kim et al.

ORGANIC LETTERS (2015)

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A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization

Joydey K. Laha et al.

ORGANIC LETTERS (2015)

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Transition-Metal-Catalyzed Site-Selective C-H Functionalization of Quinolines beyond C2 Selectivity

Tomohiro Iwai et al.

ACS CATALYSIS (2015)

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Perfluorobutyl iodide-assisted direct cyanomethylation of azoles and phenols with acetonitrile

Juan Zhang et al.

RSC ADVANCES (2015)

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Palladium-catalyzed direct alkenylation of 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-ones using oxygen as the oxidant

Junliang Lv et al.

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Regioselective palladium(ii)-catalyzed aerobic oxidative Heck-type C3 alkenylation of sulfocoumarins

Namhoon Kim et al.

ORGANIC CHEMISTRY FRONTIERS (2015)

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Access to β-Lactams by Enantioselective Palladium(0)-Catalyzed C(sp3)-H Alkylation

Julia Pedroni et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Iron- Catalyzed 1,2-Addition of Perfluoroalkyl Iodides to Alkynes and Alkenes

Tao Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Direct Olefination of Fluorinated Benzothiadiazoles: A New Entry to Optoelectronic Materials

Yu-Lan Xiao et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Reactions of Pd and Pt Complexes with Molecular Oxygen

Margaret L. Scheuermann et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Synthesis of 1-Indanols and 1-Indanamines by Intramolecular Palladium(0)-Catalyzed C(sp3)-H Arylation: Impact of Conformational Effects

Simon Janody et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Palladium-Catalyzed Meta-Selective C-H Bond Activation with a Nitrile-Containing Template: Computational Study on Mechanism and Origins of Selectivity

Yun-Fang Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Tuning Reactivity and Site Selectivity of Simple Arenes in C-H Activation: Ortho-Arylation of Anisoles via Arene-Metal pi-Complexation

Paolo Ricci et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Pd-Catalyzed Aerobic Oxidative Coupling of Arenes: Evidence for Transmetalation between Two Pd(II)-Aryl Intermediates

Dian Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Non-innocent Additives in a Palladium(II)-Catalyzed C-H Bond Activation Reaction: Insights into Multimetallic Active Catalysts

Megha Anand et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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6-Perfluoroalkylated Phenanthridines via Radical Perfluoroalkylation of Isonitriles

Bo Zhang et al.

ORGANIC LETTERS (2014)

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Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes

Shaohua Wang et al.

TETRAHEDRON LETTERS (2014)

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An organic cation as a silver(I) analogue for the arylation of sp2 and sp3 C-H bonds with iodoarenes

Carlos Arroniz et al.

CHEMICAL SCIENCE (2014)

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Pd-catalyzed dehydrogenative cross-coupling of pyridine-N-oxides with uracils

Ebrahim Kianmehr et al.

RSC ADVANCES (2014)

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Understanding the reaction mechanisms of Pd-catalysed oxidation of alcohols and domino oxidation-arylation reactions using phenyl chloride as an oxidant

Yang Li et al.

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Palladium-catalyzed direct C-3 oxidative alkenylation of phosphachromones

Dongjin Kang et al.

CHEMICAL COMMUNICATIONS (2013)

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Oxidant controlled Pd-catalysed selective oxidation of primary alcohols

Chao Liu et al.

CHEMICAL COMMUNICATIONS (2013)

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Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation

Yi-Yun Yu et al.

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Regioselective palladium-catalyzed olefination of coumarins via aerobic oxidative Heck reactions

Minsik Min et al.

CHEMICAL COMMUNICATIONS (2013)

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Synthesis of Conjugated Dienes via a Biomimetic Aerobic Oxidative Coupling of Two CvinylH Bonds

Nicolas Gigant et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

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Direct alkenylation of non-aromatic enamides via palladium-catalyzed oxidative coupling: Synthetic developments and applications

Nicolas Gigant et al.

COMPTES RENDUS CHIMIE (2013)

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Room-Temperature Direct Alkenylation of 5-Pyrazolones

Yiwen Yang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

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Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C-H Bonds

Enrico T. Nadres et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

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Developing Ligands for Palladium(II)-Catalyzed C-H Functionalization: Intimate Dialogue between Ligand and Substrate

Keary M. Engle et al.

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Controllable Direct Arylation: Fast Route to Symmetrical and Unsymmetrical 4,7-Diaryl-5,6-difluoro-2,1,3-benzothiadiazole Derivatives for Organic Optoelectronic Materials

Junxiang Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Arene-Metal π-Complexation as a Traceless Reactivity Enhancer for C-H Arylation

Paolo Ricci et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Palladium-Catalyzed C-2 Selective Arylation of Quinolines

Xiaoyu Ren et al.

ORGANIC LETTERS (2013)

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Role of Mono-N-protected Amino Acid Ligands in Palladium(II)-Catalyzed Dehydrogenative Heck Reactions of Electron-Deficient (Hetero)arenes: Experimental and Computational Studies

Xuefeng Cong et al.

ORGANOMETALLICS (2013)

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Direct C3-alkenylation of pyridin-4(1H)-one via oxidative Heck coupling

Guangling Zhang et al.

TETRAHEDRON (2013)

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Dual C-H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides

Xiao-Pu Fu et al.

TETRAHEDRON (2013)

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Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes

Chun-Yang He et al.

CHEMICAL SCIENCE (2013)

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Pd-catalyzed oxidative C-H/C-H cross-coupling of pyridines with heteroarenes

Bo Liu et al.

CHEMICAL SCIENCE (2013)

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Palladium(II)-Catalyzed Cyclization Reaction of 2-(Alk-2′-ynyloxy)benzonitriles or 2-(Alk-2′-ynylamino)benzonitriles: A Facile Way to 2H-Chromene and 1,2-Dihydroquinoline Derivatives

Guoqin Xi et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

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Palladium-Catalyzed C-2 Selective C-H Olefination of Pyridines

Ping Wen et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

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Synthesis of Hexahydroindoles by Intramolecular Csp3-H Alkenylation: Application to the Synthesis of the Core of Aeruginosins

Julien Sofack-Kreutzer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Palladium-Catalyzed Dehydrogenation/Oxidative Cross-Coupling Sequence of beta-Heteroatom-Substituted Ketones

Youngtaek Moon et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Pd(II)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage

Ziyuan Li et al.

CHEMICAL COMMUNICATIONS (2012)

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Palladium-catalyzed direct arylation of benzoxazoles with unactivated simple arenes

Ge Wu et al.

CHEMICAL COMMUNICATIONS (2012)

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Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes

Minsik Min et al.

CHEMICAL COMMUNICATIONS (2012)

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A facile route to isoflavone quinones via the direct cross-coupling of chromones and quinones

Youngtaek Moon et al.

CHEMICAL COMMUNICATIONS (2012)

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Kinetico-mechanistic studies of cyclometalating C-H bond activation reactions on Pd(II) and Rh(II) centres: The importance of non-innocent acidic solvents in the process

Jaume Granell et al.

DALTON TRANSACTIONS (2012)

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Analysis of the Palladium-Catalyzed (Aromatic)C-H Bond Metalation-Deprotonation Mechanism Spanning the Entire Spectrum of Arenes

Serge I. Gorelsky et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

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C-H Bond Functionalization Under Metalation-Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-a]pyrazine

Sankar K. Guchhait et al.

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Allylic Carbon-Carbon Double Bond Directed Pd-Catalyzed Oxidative ortho-Olefination of Arenes

Parthasarathy Gandeepan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Activation of remote meta-C-H bonds assisted by an end-on template

Dasheng Leow et al.

NATURE (2012)

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Palladium-Catalyzed C-H Functionalization Using Guanidine as a Directing Group: Ortho Arylation and Olefination of Arylguanidines

Jiaan Shao et al.

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A Sequential Pd/Norbornene-Catalyzed Process Generates o-Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6H-Dibenzopyrans by C-O Ring Closure

Elena Motti et al.

ORGANIC LETTERS (2012)

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Palladium(II)-Catalyzed Direct Alkenylation of Nonaromatic Enamides

Nicolas Gigant et al.

ORGANIC LETTERS (2012)

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Transition-State Metal Aryl Bond Stability Determines Regioselectivity in Palladium Acetate Mediated C-H Bond Activation of Heteroarenes

Alban Petit et al.

ORGANIC LETTERS (2012)

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Palladium-Catalyzed Intermolecular C3 Alkenylation of Indoles Using Oxygen as the Oxidant

Wen-Liang Chen et al.

ORGANIC LETTERS (2012)

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Palladium-Catalyzed Aerobic Dehydrogenative Cross-Coupling of Polyfluoroarenes with Thiophenes: Facile Access to Polyfluoroarene-Thiophene Structure

Chun-Yang He et al.

ORGANOMETALLICS (2012)

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Reactivity and Regioselectivity of Palladium-Catalyzed Direct Arylation in Noncooperative and Cooperative Processes

Serge I. Gorelsky

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Tuning the Regioselectivity of Palladium-Catalyzed Direct Arylation of Azoles by Metal Coordination

Serge I. Gorelsky

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Mechanistic Insight into the Regioselective Palladation of Indole Derivatives: Tetranuclear Indolyl Palladacycles with High C2-Pd or C3-Pd Bond Selectivity

Yang Li et al.

ORGANOMETALLICS (2012)

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β-Elimination competitions leading to C=C bonds from alkylpalladium intermediates

Jean Le Bras et al.

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Palladium(II)-catalyzed oxidative homo-coupling of 1,3-dimethyluracil derivatives

Ko Hoon Kim et al.

TETRAHEDRON LETTERS (2012)

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Palladium-catalyzed oxidative arylation of chromones via a double C-H activation: an expedient approach to flavones

Ko Hoon Kim et al.

TETRAHEDRON LETTERS (2012)

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Palladium-catalyzed selective oxidative olefination and arylation of 2-pyridones

Yuye Chen et al.

CHEMICAL SCIENCE (2012)

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Speciation of Pd(OAc)2 in ligandless Suzuki-Miyaura reactions

Luis A. Adrio et al.

CATALYSIS SCIENCE & TECHNOLOGY (2012)

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Regioselective Cross-Dehydrogenative Coupling of Chromones and Non-Activated Arenes

Minsik Min et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Increasing synthetic efficiency via direct C-H functionalization: formal synthesis of an inhibitor of botulinum neurotoxin

Shathaverdhan Potavathri et al.

CHEMICAL COMMUNICATIONS (2011)

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Intermolecular Dehydrogenative Heck Reactions

Jean Le Bras et al.

CHEMICAL REVIEWS (2011)

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Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope

Lutz Ackermann

CHEMICAL REVIEWS (2011)

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(N-Heterocyclic Carbene)-Pd-Catalyzed Anaerobic Oxidation of Secondary Alcohols and Domino Oxidation-Arylation Reactions

Brant Landers et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

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Regioselective Direct C-H Arylations of Protected Uracils. Synthesis of 5-and 6-Aryluracil Bases

Miroslava Cernova et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

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Ligand-Promoted C-3 Selective C-H Olefination of Pyridines with Pd Catalysts

Mengchun Ye et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Assessment of the Intermediacy of Arylpalladium Carboxylate Complexes in the Direct Arylation of Benzene: Evidence for C-H Bond Cleavage by Ligandless Species

Yichen Tan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Ligand-Promoted C3-Selective Arylation of Pyridines with Pd Catalysts: Gram-Scale Synthesis of (±)-Preclamol

Mengchun Ye et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

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Palladium(II)-Catalyzed Direct Intermolecular Alkenylation of Chromones

Donghee Kim et al.

ORGANIC LETTERS (2011)

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Double C-H Activation: The Palladium-Catalyzed Direct C-Arylation of Xanthines with Arenes

Chandi C. Malakar et al.

ORGANIC LETTERS (2011)

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Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides

Bo Ram Park et al.

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Palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil with aryl bromides: an electrophilic metalation-deprotonation with electrophilic arylpalladium intermediate

Ko Hoon Kim et al.

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Emergence of Palladium(IV) Chemistry in Synthesis and Catalysis

Petr Sehnal et al.

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Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Pathway

David Lapointe et al.

CHEMISTRY LETTERS (2010)

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Highly Effective Pd-Catalyzed ortho Olefination of Acetanilides: Broad Substrate Scope and High Tolerability

Byung Seok Kim et al.

CHEMISTRY-AN ASIAN JOURNAL (2010)

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Pd-II-Catalyzed Highly Selective Arylation of Allyl Esters via C-H Functionalization of Unreactive Arenes with Retention of the Traditional Leaving Group

Delin Pan et al.

CHEMISTRY-AN ASIAN JOURNAL (2010)

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One-Pot Syntheses of α,β-Unsaturated Carbonyl Compounds through Palladium-Mediated Dehydrogenation of Ketones, Aldehydes, Esters, Lactones and Amides

Jacques Muzart

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2010)

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Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles

Mitsuru Miyasaka et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Multidisciplinary

Regioselective Oxidative Arylation of Indoles Bearing N-Alkyl Protecting Groups: Dual C-H Functionalization via a Concerted Metalation-Deprotonation Mechanism

Shathaverdhan Potavathri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Pd(OAc)2 Catalyzed Olefination of Highly Electron-Deficient Perfluoroarenes

Xingang Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Ligand-Accelerated C-H Activation Reactions: Evidence for a Switch of Mechanism

Keary M. Engle et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Ortho-Arylation of O-Phenylcarbamates with Simple Arenes and Sodium Persulfate

Xiaodan Zhao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Intramolecular Palladium-Catalyzed Alkane C-H Arylation from Aryl Chlorides

Sophie Rousseaux et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Multidisciplinary

Pd(OAc)2-Catalyzed Oxidative C-H/C-H Cross-Coupling of Electron-Deficient Polyfluoroarenes with Simple Arenes

Ye Wei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

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Article Chemistry, Organic

Direct oxidative coupling of benzenes with acrylonitriles to cinnamonitriles catalyzed by Pd(OAc)(2)/HPMoV/O-2 system

Yasushi Obora et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2010)

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Article Chemistry, Organic

Switching the Regioselectivity of Direct C-H Arylation of 1,3-Dimethyluracil

Miroslava Cernova et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2009)

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Review Chemistry, Organic

Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds

Benoit Liegault et al.

JOURNAL OF ORGANIC CHEMISTRY (2009)

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Article Chemistry, Physical

Estimation of Molecular Acidity via Electrostatic Potential at the Nucleus and Valence Natural Atomic Orbitals

Shubin Liu et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2009)

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Pd(II)-Catalyzed Olefination of Electron-Deficient Arenes Using 2,6-Dialkylpyridine Ligands

Yang-Hui Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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Article Chemistry, Organic

Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes

Chahinez Aouf et al.

ORGANIC LETTERS (2009)

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Review Chemistry, Organic

N,N-Dimethylformamide: much more than a solvent

Jacques Muzart

TETRAHEDRON (2009)

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Article Chemistry, Organic

Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C-H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

Junwon Kim et al.

TETRAHEDRON LETTERS (2009)

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Article Chemistry, Physical

Accurate calculation of the pKa of trifluoroacetic acid using high-level ab initio calculations

Mansoor Namazian et al.

CHEMICAL PHYSICS LETTERS (2008)

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Review Chemistry, Multidisciplinary

Ag-mediated reactions: Coupling and heterocyclization reactions

Jean-Marc Weibel et al.

CHEMICAL REVIEWS (2008)

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Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air:: Reaction development and scope

Benoit Liegault et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

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Room temperature and phosphine free palladium catalyzed direct C-2 arylation of indoles

Nathalie Lebrasseur et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Analysis of the concerted metalation-deprotonation mechanism in palladium-catalyzed direct arylation across a broad range of aromatic substrates

Serge I. Gorelsky et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Review Chemistry, Multidisciplinary

Synthesis of Benzocyclobutenes by Palladium-Catalyzed C-H Activation of Methyl Groups: Method and Mechanistic Study

Manon Chaumontet et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

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Article Chemistry, Multidisciplinary

Oxidative arylation of ethylene with benzene catalyzed by Pd(OAc)(2)/heteropoly acid/O-2 system

Tomoyuki Yamada et al.

NEW JOURNAL OF CHEMISTRY (2008)

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Article Chemistry, Organic

Benzylic C-H activation and C-O bond formation via aryl to benzylic 1,4-palladium migrations

Tanay Kesharwani et al.

TETRAHEDRON (2008)

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Article Chemistry, Organic

Mild and efficient palladium-catalyzed intramolecular direct arylation reactions

Marc Lafrance et al.

TETRAHEDRON (2008)

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Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles

Shathaverdhan Potavathri et al.

TETRAHEDRON LETTERS (2008)

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High-yielding palladium-catalyzed intramolecular alkane arylation: Reaction development and mechanistic studies

Marc Lafrance et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling

David R. Stuart et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Chemistry, Organic

Pd-catalyzed reduction of aryl halides using dimethylformamide as the hydride source

Anna Maria Zawisza et al.

TETRAHEDRON LETTERS (2007)

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Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation:: Substituent effects

Domingo Garcia-Cuadrado et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Multidisciplinary Sciences

The catalytic cross-coupling of unactivated arenes

David R. Stuart et al.

SCIENCE (2007)

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Agostic interactions in transition metal compounds

Maurice Brookhart et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2007)

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Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design

Marc Lafrance et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Highly regioselective catalytic oxidative coupling reactions: Synthetic and mechanistic investigations

Kami L. Hull et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Molecular oxygen to regenerate PdII active species

Jacques Muzart

CHEMISTRY-AN ASIAN JOURNAL (2006)

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Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion

Hung-Yat Thu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Catalytic intermolecular direct arylation of perfluorobenzenes

Marc Lafrance et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation

D García-Cuadrado et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions

LC Campeau et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Mechanistic questions about the reaction of molecular oxygen with palladium in oxidase catalysis

Keith M. Gligorich et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

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Computational study of the mechanism of cyclometalation by palladium acetate

DL Davies et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Review Chemistry, Organic

Palladium-catalysed reactions of alcohols. Part D: Rearrangements, carbonylations, carboxylations and miscellaneous reactions

J Muzart

TETRAHEDRON (2005)

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Oxidative coupling of benzenes with α,β-unsaturated aldehydes by the Pd(OAc)2[molybdovanadophosphoric acid/O2 system

T Yamada et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Palladium-catalysed reactions of alcohols. Part C: Formation of ether linkages

J Muzart

TETRAHEDRON (2005)

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Direct palladium-catalyzed C-2 and C-3 arylation of indoles: A mechanistic rationale for regioselectivity

BS Lane et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ

X Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

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Article Chemistry, Organic

Pd(OAc)2-catalyzed oxidative coupling reaction of benzenes with olefins in the presence of molybdovanadophosphoric acid under atmospheric dioxygen and air

M Tani et al.

JOURNAL OF ORGANIC CHEMISTRY (2004)

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Regioselective Pd-catalyzed alkylative lactonizations of 4-hydroxy-2-alkynecarboxylates with organoboronic acids

CH Oh et al.

TETRAHEDRON LETTERS (2004)

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Elucidating the significance of β-hydride elimination and the dynamic role of acid/base chemistry in a palladium-catalyzed aerobic oxidation of alcohols

JA Mueller et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

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Article Chemistry, Inorganic & Nuclear

Formation of anionic palladium(0) complexes ligated by the trifluoroacetate ion and their reactivity in oxidative addition

C Amatore et al.

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2004)

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Article Biochemistry & Molecular Biology

Palladium-catalyzed oxidation of benzylated aldose hemiacetals to lactones

A Bessmertnykh et al.

CARBOHYDRATE RESEARCH (2004)

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Review Chemistry, Organic

Palladium-catalysed oxidation of primary and secondary alcohols

J Muzart

TETRAHEDRON (2003)

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Productive utilization of chlorobenzene: Palladium-catalyzed selective oxidation of alcohols

AS Guram et al.

ORGANIC LETTERS (2003)

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Toward waste-free production of Heck products with a catalytic palladium system under oxygen

M Dams et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2003)

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Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis

MA Campo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

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Second- and inverse order pathways in the mechanism of orthopalladation of primary amines

SA Kurzeev et al.

INORGANICA CHIMICA ACTA (2002)

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Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature

MDK Boele et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

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Article Chemistry, Multidisciplinary

Pd-catalysed arylation of propan-1-ol and derivatives: oxidative role of the arylating agent

L Bagnell et al.

CHEMICAL COMMUNICATIONS (2001)

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Review Chemistry, Inorganic & Nuclear

Trans-effects in octahedral transition metal complexes

BJ Coe et al.

COORDINATION CHEMISTRY REVIEWS (2000)

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