Regio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis

Article Chemistry, Multidisciplinary

Minimization of Back-Electron Transfer Enables the Elusive sp3 C-H Functionalization of Secondary Anilines

Huaibo Zhao et al.

Summary: The presence of an exogenous alkylamine in photoredox catalysis can minimize back-electron transfer in anilines and facilitate the generation of alpha-anilinoalkyl radicals, enabling divergent sp(3) C-H functionalization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α-Arylated Amines and N-Heterocycles

Ana Koperniku et al.

Summary: The zirconium catalyzed hydroaminoalkylation of alkenes with N-aryl- and sterically demanding N-alkyl-alpha-arylated secondary amines using commercially available Zr(NMe2)(4) is reported. The catalyst is compatible with challenging alpha-heteroarylated amines and functionalized alkene substrates, providing a new disconnection strategy for selectively substituted saturated alpha-arylated heterocycles.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Titanium-Catalyzed Intermolecular Hydroaminoalkylation of Alkenes with Tertiary Amines

Dennis Geik et al.

Summary: A novel cationic titanium catalyst system was developed for intermolecular hydroaminoalkylation of alkenes with tertiary alkylamines, resulting in excellent regioselectivity towards branched products. Interestingly, alpha-C-H bond activation was observed not only at N-methyl but also at N-methylene groups for selected amines.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Physical

Dual Palladium/Photoredox-Catalyzed Enantioselective and Regioselective Decarboxylative Hydroaminoalkylation of Allenes

Jun Zheng et al.

Summary: A dual palladium/photoredox-catalyzed regio- and enantioselective decarboxylative hydroaminoalkylation of allenes with amino acids was reported. This method allows efficient access to protected vinyl 1,2-amino ethers with high levels of branched and enantioselectivity.

ACS CATALYSIS (2021)

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Article Multidisciplinary Sciences

Anti-Markovnikov hydro(amino)alkylation of vinylarenes via photoredox catalysis

Zhao Wu et al.

Summary: The use of photoredox catalysis allows for the hydroalkylation and hydroaminoalkylation of electronically diverse vinylarenes, providing a new approach for accessing valuable compounds with pharmacophores. The reaction's substrate scope was evaluated through numerous examples, demonstrating its synthetic utility and potential applications in organic synthesis.

NATURE COMMUNICATIONS (2021)

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Article Multidisciplinary Sciences

Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines

Xiao-Biao Yan et al.

Summary: The authors demonstrate a method to add alkanes with an amino functionality to olefins using a nickel catalyst that utilizes the amine itself as the hydride source, eliminating the need for an external hydride reagent. This approach allows for the production of valuable, complex structural motifs and chiral alpha-branched amines in organic synthesis. Additionally, the use of a P-chiral ligand further enhances the catalytic efficiency of the reaction.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Physical

Ureate Titanium Catalysts for Hydroaminoalkylation: Using Ligand Design to Increase Reactivity and Utility

Manfred Manssen et al.

Summary: Hydroaminoalkylation involves the catalytic synthesis of amines from easily accessible amine and alkene feedstocks, utilizing a cost-efficient titanium catalyst with high catalytic activity and regioselectivity. The synthesized amine-containing monomers are suitable for generating amine-containing materials and building blocks for medicinal chemistry.

ACS CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Direct, Catalytic α-Alkylation of N-Heterocycles by Hydroaminoalkylation: Substrate Effects for Regiodivergent Product Formation

Rebecca C. DiPucchio et al.

Summary: This study presents a method for the direct alkylation of unprotected amine heterocycles using an early transition-metal system, allowing for short reaction times and selective formation of branched reaction products in most cases. By avoiding the use of high loadings of precious metal catalysts, this method offers a more efficient approach to alkylate saturated N-heterocycles.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines

Hannah E. Askey et al.

Summary: This study presents a method for the direct, modular, and sustainable preparation of alpha-(di)substituted gamma-arylamines using organophotoredox catalysis. The method is versatile, tolerating a broad range of functionalities, and can be scaled up to multigram quantities in continuous flow.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Hong-Hao Zhang et al.

Summary: A highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates has been demonstrated using cooperative palladium and photoredox catalysis, providing a straightforward protocol for the stereoselective construction of C(sp(3))-C(sp(3)) bonds. This method enables the synthesis of a series of C-2-symmetrical chiral 1,5-dienes with excellent enantioselectivities, diastereoselectivities, and regioselectivities, which can be used as chiral ligands in asymmetric synthesis and transformed into other valuable chiral ligands.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines

Natalia A. Larionova et al.

Summary: A photocatalytic method for alpha-selective hydroaminoalkylation of cinnamate esters has been developed, demonstrating regioselective addition of alpha-aminoalkyl radicals to unsaturated esters. The study expanded the scope to include styrenes with anti-Markovnikov selectivity, emphasizing the importance of the aromatic group at the beta-position. Simple scale-up under continuous flow conditions highlights the practicality of the method.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling

Raphael K. Klake et al.

Summary: A new catalytic enantioselective addition method utilizing copper-catalyzed reductive coupling to add N-substituted allyl equivalents to ketones has been developed, accessing important chiral 1,2-aminoalcohol synthons with high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed, including the identification of a reversible ketone allylation step previously unreported in copper-catalyzed reductive coupling.

ORGANIC LETTERS (2021)

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Review Chemistry, Multidisciplinary

Radical philicity and its role in selective organic transformations

Faeze Parsaee et al.

Summary: Radical philicity, the ability of radicals to act as nucleophiles or electrophiles, is an important concept in organic chemistry. Traditionally, radicals are considered electron deficient, but the term "electron deficient" can imply electrophilicity in modern literature. This discrepancy has led to misconceptions about radical behavior, as many radicals actually exhibit nucleophilic behavior. This review aims to guide the understanding and prediction of radical philicity, demonstrating that not all radicals behave as electrophiles.

NATURE REVIEWS CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Fast Titanium-Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine

Jens Bielefeld et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Review Chemistry, Multidisciplinary

New Strategies for the Transition-Metal Catalyzed Synthesis of Aliphatic Amines

Aaron Trowbridge et al.

CHEMICAL REVIEWS (2020)

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Article Chemistry, Multidisciplinary

Iridium(I)-Catalyzed alpha-C(sp(3))-H Alkylation of Saturated Azacycles

Pritha Verma et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Photocatalytic α-Tertiary Amine Synthesis via C-H Alkylation of Unmasked Primary Amines

Alison S. H. Ryder et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Physical

Enantioselective α-Allylation of Anilines Enabled by a Combined Palladium and Photoredox Catalytic System

Hong-Hao Zhang et al.

ACS CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Regioselective, Photocatalytic α-Functionalization of Amines

Lingying Leng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Cyclic Ureate Tantalum Catalyst for Preferential Hydroaminoalkylation with Aliphatic Amines: Mechanistic Insights into Substrate Controlled Reactivity

Pargol Daneshmand et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Multidisciplinary

Transition metal-catalysed allylic functionalization reactions involving radicals

Huan-Ming Huang et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Article Chemistry, Multidisciplinary

Introduction of a 7-aza-6-MeO-indoline auxiliary in Lewis-acid/photoredox cooperative catalysis: highly enantioselective aminomethylation of α,β-unsaturated amides

Santosh K. Pagire et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Multidisciplinary

Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3 coupling of carboxylic acids and π-electrophiles

Kaitie C. Cartwright et al.

CHEMICAL SCIENCE (2020)

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Review Chemistry, Multidisciplinary

Light Up the Transition Metal-Catalyzed Single-Electron Allylation

Mao-Mao Zhang et al.

TRENDS IN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines

Kangning Cao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Review Chemistry, Organic

Catalytic and Enantioselective Diels-Alder Reaction of Siloxydienes

Shinji Harada et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer

Kim Spielmann et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Review Chemistry, Multidisciplinary

Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling

John A. Milligan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Multidisciplinary

Synthesis of beta-Substituted gamma-Aminobutyric Acid Derivatives through Enantioselective Photoredox Catalysis

Jiajia Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Multidisciplinary

2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones

Kangnan Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

Xiang Shen et al.

CHEMICAL SCIENCE (2018)

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Article Multidisciplinary Sciences

Multicomponent synthesis of tertiary alkylamines by photocatalytic olefin-hydroaminoalkylation

Aaron Trowbridge et al.

NATURE (2018)

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Article Chemistry, Multidisciplinary

Direct α-alkylation of primary aliphatic amines enabled by CO2 and electrostatics

Juntao Ye et al.

NATURE CHEMISTRY (2018)

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Article Chemistry, Applied

Iridium-Catalyzed Sequential sp3 C-H Alkylation of an N-Methyl Group with Alkenes Towards the Synthesis of α-Substituted Amines

Hiroshi Hattori et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Enantioselective Allylic Alkylation with 4-Alkyl-1,4-dihydropyridines Enabled by Photoredox/Palladium Cocatalysis

Hong-Hao Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Multidisciplinary

Early transition metal-catalyzed C-H alkylation: hydroaminoalkylation for C-sp(3)-C-sp(3) bond formation in the synthesis of selectively substituted amines

P. M. Edwards et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Multidisciplinary

A Mild Hydroaminoalkylation of Conjugated Dienes Using a Unified Cobalt and Photoredox Catalytic System

Scott M. Thullen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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Article Chemistry, Multidisciplinary

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals

Mattia Silvi et al.

NATURE CHEMISTRY (2017)

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Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles

Anh T. Tran et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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Article Chemistry, Multidisciplinary

A visible-light-activated rhodium complex in enantioselective conjugate addition of α-amino radicals with Michael acceptors

Shao-Xia Lin et al.

CHEMICAL COMMUNICATIONS (2017)

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Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Alkylation Using Alkenes

Zhe Dong et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Multidisciplinary

Asymmetric Radical-Radical Cross-Coupling through Visible-Light-Activated Iridium Catalysis

Chuanyong Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Review Chemistry, Multidisciplinary

Synthetic Utilization of α-Aminoalkyl Radicals and Related Species in Visible Light Photoredox Catalysis

Kazunari Nakajima et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

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Review Chemistry, Multidisciplinary

Dual Catalysis Strategies in Photochemical Synthesis

Kazimer L. Skubi et al.

CHEMICAL REVIEWS (2016)

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Article Chemistry, Medicinal

2-Chloro-4-[[(1R,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrile: A Transdermal Selective Androgen Receptor Modulator (SARM) for Muscle Atrophy

Ashraf Saeed et al.

JOURNAL OF MEDICINAL CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

Catalytic, Enantioselective Addition of Alkyl Radicals to Alkenes via Visible-Light-Activated Photoredox Catalysis with a Chiral Rhodium Complex

Haohua Huo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Multidisciplinary Sciences

Asymmetric catalytic formation of quaternary carbons by iminium ion trapping of radicals

John J. Murphy et al.

NATURE (2016)

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Article Chemistry, Multidisciplinary

Enantioselective sp(3) C-H alkylation of gamma-butyrolactam by a chiral Ir(I) catalyst for the synthesis of 4-substituted gamma-amino acids

Yu-ki Tahara et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Chemistry, Multidisciplinary

Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms

Simon B. Lang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

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Article Chemistry, Multidisciplinary

Redox-Neutral α-Allylation of Amines by Combining Palladium Catalysis and Visible-Light Photoredox Catalysis

Jun Xuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Article Chemistry, Medicinal

Discovery of pyrrolo[1,2-b]pyridazine-3-carboxamides as Janus kinase (JAK) inhibitors

James J. -W. Duan et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2014)

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Article Chemistry, Multidisciplinary

Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin

Lingling Chu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Multidisciplinary

Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis

Simon B. Lang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Organic

Ruthenium(II)-Catalyzed C(sp3)-H α-Alkylation of Pyrrolidines

Marvin Schinkel et al.

ORGANIC LETTERS (2014)

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Article Chemistry, Organic

Unique Regioselectivity in the C(sp3)-H α-Alkylation of Amines: The Benzoxazole Moiety as a Removable Directing Group

Guenther Lahm et al.

ORGANIC LETTERS (2014)

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Article Chemistry, Organic

Hydroaminoalkylation: Early-Transition-Metal-Catalyzed α-Alkylation of Amines

Eugene Chong et al.

SYNTHESIS-STUTTGART (2014)

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Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

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Article Chemistry, Multidisciplinary

The Mechanism of Hydroaminoalkylation Catalyzed by Group 5 Metal Binaphtholate Complexes

Alexander L. Reznichenko et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Article Chemistry, Multidisciplinary

Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition to Electron-Deficient Alkenes Using Photoredox Catalysts

Yoshihiro Miyake et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

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Article Chemistry, Organic

Ir(I)-Catalyzed Enantioselective Secondary sp3 C-H Bond Activation of 2-(Alkylamino)pyridines with Alkenes

Shiguang Pan et al.

ORGANIC LETTERS (2011)

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Article Chemistry, Inorganic & Nuclear

Group 5 Metal Binaphtholate Complexes for Catalytic Asymmetric Hydroaminoalkylation and Hydroamination/Cyclization

Alexander L. Reznichenko et al.

ORGANOMETALLICS (2011)

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Article Chemistry, Multidisciplinary

Highly enantioselective hydroaminoalkylation of secondary amines catalyzed by group 5 metal amides with chiral biarylamidate ligands

Guofu Zi et al.

CHEMICAL COMMUNICATIONS (2010)

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Article Chemistry, Multidisciplinary

Tantalum-Amidate Complexes for the Hydroaminoalkylation of Secondary Amines: Enhanced Substrate Scope and Enantioselective Chiral Amine Synthesis

Patrick Eisenberger et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

Catalytic Hydroaminoalkylation

Peter W. Roesky

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Article Chemistry, Multidisciplinary

Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

Shin-ya Tosaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

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Article Multidisciplinary Sciences

Catalytic enantioselective reactions driven by photoinduced electron transfer

A Bauer et al.

NATURE (2005)

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Article Chemistry, Multidisciplinary

Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes

N Chatani et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

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Regio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis

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