☆ 4.6 Review

Recent advances in ligand-enabled palladium-catalyzed divergent synthesis

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

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Article Chemistry, Organic

Palladium-Catalyzed Chemodivergent Carbonylation of ortho-Bromoarylimine to Biisoindolinones and Spiroisoindolinones

Jiaqi Yan et al.

Summary: A palladium-catalyzed carbonylative cyclization reaction of ortho-bromoarylimines is reported, allowing for the chemodivergent synthesis of functionalized biisoindolinones and spirocyclic isoindolinones. By switching the reaction temperatures and ligands, either product could be selectively obtained, and the biisoindolinone products could be easily achieved with catalyst loadings as low as 0.05 mol%. Further transformation of the biisoindolinone product is also described, providing a novel and concise approach to the biisoindoline diamine ligand.

JOURNAL OF ORGANIC CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Diastereodivergent cis- and trans-fused [4 + 2] annulations of cyclic 1,3-dienes and 1-azadienes via ligand-controlled palladium catalysis

Yuan Hu et al.

Chemical Science (2023)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Alkyne Hydrocyanation toward Ligand-Controlled Stereodivergent Synthesis of (E)- and (Z)-Trisubstituted Acrylonitriles

Jinguo Long et al.

Summary: A palladium-catalyzed hydrocyanation of propiolamides for the stereodivergent synthesis of trisubstituted acrylonitriles is described. The method can tolerate various primary, secondary, and tertiary propiolamides. The selection of a suitable ligand is crucial for the success of this stereodivergent process. Control experiments indicate the intermediacy of E-acrylonitriles, which undergo isomerization to form Z-acrylonitriles. Density functional theory calculations suggest that the bidentate ligand L2 enables a feasible cyclometallation/isomerization pathway for the E to Z isomerization, while the monodentate ligand L1 inhibits the isomerization, leading to divergent stereoselectivity. The usefulness of this method is demonstrated by the facile derivatization of products to give various E- and Z-trisubstituted alkenes. Additionally, the E- and Z-acrylonitrile products have been successfully employed in cycloaddition reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Multidisciplinary

Ligand-Dictated Regiodivergent Allylic Functionalizations via Palladium-Catalyzed Remote Substitution

Xin Wang et al.

Summary: This study describes feasible protocols to achieve regiodivergent allylic C-H functionalizations via palladium-catalyzed remote substitution, which provides a novel strategy for the seldomly studied migratory Tsuji-Trost reaction. Dictated by a suitable ligand, a process involving 4,3-hydrofunctionalization of the generated conjugated diene intermediate via metal walking is observed with generally >20 : 1 regioselectivity. A major route is also found for 1,4-hydrofunctionalization with a newly synthesized electron-rich bisphosphine ligand.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Article Chemistry, Multidisciplinary

Recent advances in annulations enabled by nucleophilic Lewis base/metal dual catalysis

Qian Wang et al.

Summary: Metal/nucleophilic Lewis base dual catalysis has been recognized as a reliable and promising strategy for finishing ideal organic synthesis. This new strategy expands the synthetic utility of chemical transformations by leveraging additional activation modes and has made considerable progress in the synthesis of a wide range of heterocyclic and biologically active compounds. In this review, the comprehensive and updated advances of metal/nucleophilic Lewis base dual catalytic annulation reactions are described, along with the highlighting of the related mechanism and application in natural product total synthesis.

CHINESE CHEMICAL LETTERS (2023)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes

Songjia Fang et al.

Summary: This study reports a palladium-catalyzed sequential tandem cyclization reaction that efficiently assembles various 3-halo-1,2,5-triarylpyrrole derivatives through the reaction of two molecular haloalkynes and one molecular N-alkylanilines. The reaction conveniently transforms two carbon-carbon triple bonds and one carbon-halogen bond in one step, showcasing high chemo- and regioselectivities.

CHINESE JOURNAL OF CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Catalyst-Controlled Annulations of Strained Cyclic Allenes with π-Allylpalladium Complexes

Dominick C. Witkowski et al.

Summary: This study reports the annulations of strained cyclic allenes with in situ-generated pi-allylpalladium species, resulting in the synthesis of heterocyclic and sp3-rich polycyclic scaffolds with high selectivity. The products bear two or three new stereocenters, making them highly valuable for complex scaffold assembly. This research encourages further development in fragment couplings that rely on transition metal catalysis and strained cyclic allenes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

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Article Chemistry, Organic

Palladium-Catalyzed Hydroalkoxycarbonylation and Hydroxycarbonylation of Cyclopent-3-en-1-ols: Divergent Synthesis of Bridged Cyclic Lactones and β,γ-Unsaturated Carboxylic Acids

Ming Chen et al.

Summary: In this work, a palladium-catalyzed hydroalkoxycarbonylation and hydroxycarbonylation of cyclopent-3-en-1-ols is reported, which enables the synthesis of bridged bicyclic lactones and beta,gamma-unsaturated carboxylic acid. The reactivity of cyclopent-3-en-1-ols is controlled by the palladium catalyst and ligands. The reaction is additive-free and exhibits a broad substrate scope, allowing access to valuable synthetic and medical intermediates.

ORGANIC LETTERS (2023)

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Review Chemistry, Multidisciplinary

Ni-catalyzed ligand-controlled divergent and selective synthesis

Yang Ke et al.

Summary: Scaffold diversity is crucial for the success of compound libraries in biological screening. This review focuses on recent efforts in Ni-catalyzed divergent and selective synthesis, which generate structurally diverse molecular scaffolds using the same substrate and varying the ligand backbone under almost identical reaction conditions. The progress achieved encourages the design and development of new selective catalytic systems and reveals new modes of catalytic transformation for broader synthetic applications.

SCIENCE CHINA-CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Stereodivergent Construction of Csp3-Csp3 Bonds Bearing Vicinal Stereocenters by Synergistic Palladium and Phase-Transfer Catalysis

Jingqiang Han et al.

Summary: This paper reports a synergistic palladium/phase-transfer catalyst system that enables stereodivergent Csp(3)-Csp(3) coupling reactions between stabilized nucleophiles and 1,3-dienes. The products showed different stereochemistry and good yields. Non-covalent activation of the stabilized nucleophile was a crucial factor in achieving stereodivergence.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

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Review Chemistry, Multidisciplinary

Recent Advances in Palladium-Catalyzed [4+n] Cycloaddition of Lactones, Benzoxazinanones, Allylic Carbonates, and Vinyloxetanes

Mengyan Guo et al.

Summary: Palladium-catalyzed allylation cyclization reactions have become an important synthetic method for the construction of diverse organic compounds. This review focuses on the development of palladium-catalyzed [4 + n] cycloaddition reactions using allylic motifs, highlighting the mechanism and application of these strategies in natural product synthesis.

TOPICS IN CURRENT CHEMISTRY (2023)

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Article Chemistry, Physical

Stereodivergent construction of [6.5]-spirocycles bearing three contiguous stereogenic centers by Pd-catalyzed [4+2] annulations

Zhan-Cai Ma et al.

Summary: The synthesis of spirocyclic frameworks with multiple stereogenic centers through a single transformation is a high-priority challenge in synthetic chemistry. This study reports an unprecedented efficient stereodivergent [4+2] annulation reaction using palladium catalysts to synthesize spiropyrazolones with three contiguous stereogenic centers. Excellent diastereodivergency (up to >20:1) and enantioselectivity (up to >99% ee) have been achieved using different commercially available chiral ligands. This is the first example of employing vinyl benzoxazinanones as the palladium p-allyl precursor for stereodivergent reactions. Density functional theory (DFT) calculations provide insights into the mechanism of this stereodivergent annulation process.

CHEM CATALYSIS (2023)

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Article Chemistry, Multidisciplinary

Asymmetric Auto-Tandem Palladium Catalysis for 2,4-Dienyl Carbonates: Ligand-Controlled Divergent Synthesis

Jian-Xiang Zhu et al.

Summary: This study presents the development of a new asymmetric auto-tandem catalysis process, which allows for the synthesis of diverse compounds with excellent stereocontrol. The use of chiral ligands enables the switchable diastereodivergent synthesis, demonstrating the versatility of this auto-tandem catalysis.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Recent Advances in Lewis Base-Catalysed Chemo-, Diastereo- and Enantiodivergent Reactions of Electron-deficient Olefins and Alkynes

Yinggao Meng et al.

Summary: Lewis base catalysis provides powerful synthetic strategies for the selective construction of carbon-carbon and carbon-heteroatom bonds. The nucleophilicity and steric hindrance of Lewis base catalyst often plays a major role in catalytic reactivity and selectivity in the reaction. Tremendous progress has been made in the divergent construction of valuable motifs under Lewis base catalysis in the past decades.

CHEMICAL RECORD (2022)

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Recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides

Wei Wu et al.

Summary: This review summarizes the recent advances in the synthesis of fluoroalkylated compounds using fluoroalkyl anhydrides as reagents, aiming to provide a reference for researchers to develop new synthetic strategies and achieve large-scale preparation of fluorine-containing organic compounds.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Ligand- and Substrate-Controlled Chemodivergent Pd-Catalyzed Annulations of Cyclic β-Keto Esters with 3-Aryl-2H-azirines

Fang Xie et al.

Summary: The study presents a chemodivergent Pd-catalyzed approach for the rapid synthesis of eight-membered ring lactams, bicyclic 3,4-dihydro-2H-pyrrole derivatives, and (E)-methyl [2-(2-oxocyclohexylidene)-2-phenylethyl]carbamates with high efficiency. Chemoselectivity can be determined by adjusting the mono- or bisphosphine ligands and the substrate structure of cyclic beta-keto esters.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regiodivergent Synthesis of 1,3-Dienyl and Allyl Esters from Propargyl Esters

Mengfu Dai et al.

Summary: This study reports a catalyst-controlled, tunable, and predictable regiodivergency in transforming internal aliphatic propargyl esters into diverse products, allowing facile access to regioisomers with high regio- and stereoselectivity. This method is important for the structural diversification of bioactive molecules, enabling the rapid assembly of structural analogs of pharmaceutical candidates.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Ligand-Controlled Site- and Enantioselective Carbene Insertion into Carbon-Silicon Bonds of Benzosilacyclobutanes

Jingfeng Huo et al.

Summary: In this study, a highly efficient palladium-catalyzed carbene insertion reaction into strained Si-C bonds of benzosilacyclobutanes was reported, providing an efficient method for accessing alpha-chiral silanes. It was found that with a sterically hindered ligand, the carbene insertion occurred selectively on the C(sp(3))-Si bond of benzosilacyclobutanes with excellent site- and enantioselectivity, while selectively occurred on the C(sp(2))-Si bond with less sterically hindered ligands. The reaction mechanism, particularly the roles of chiral ligands in controlling the site-selectivity of the insertion reactions, was elucidated using hybrid density functional theory.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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A general strategy for in situ assembly of light-up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling

Xiang Li et al.

Summary: This study presents a general strategy for the in situ assembly of intramolecular charge-transfer (ICT)-based light up fluorophores via bioorthogonal Suzuki-Miyaura cross-coupling reaction. The designed fluorophores showed significant fluorescence enhancement and high fluorescence quantum yield after reaction with aryl boronic acid or boronate. They have been successfully applied in peptide conjugation, no-wash fluorogenic protein labeling, and mitochondria-selective bioorthogonal imaging in live cells.

CHINESE CHEMICAL LETTERS (2022)

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Ligand-Controlled Palladium-Catalyzed Asymmetric [4+3] and [2+3] Annulation Reactions of Spirovinylcyclopropyl Oxindoles with o-Quinone Methides

Xiyuan Zhang et al.

Summary: We report regiodivergent ligand-controlled palladium-catalyzed asymmetric cycloaddition reactions. By using different chiral ligands, the reactions can be controlled to give different reaction pathways and stereoselectivities.

ORGANIC LETTERS (2022)

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Use of (E,E)-Dienoic Acids as Switchable (E,E)- and (Z,E)-Dienyl Anion Surrogates via Ligand-Controlled Palladium Catalysis

Shun-Zhong Tan et al.

Summary: This study demonstrates the application limitation of carboxylic acids as carbon-based nucleophiles, and proposes a method using free (E,E)-2,4-dienoic acids to form complexes with Pd(0) and undergo selective addition reactions with imines to produce dienylated products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Ligand-Controlled Palladium-Catalyzed Regiodivergent Defluorinative Allylation of gem-Difluorocyclopropanes via σ-Bond Activation

Lei Wu et al.

Summary: Monofluoroalkenes are important and versatile components in pharmacologically relevant molecules. A method for the selective construction of these compounds through regiodivergent cross-coupling of gem-difluorocyclopropanes with allylboronates is reported. The use of different ligands allows for control of the linear or branched selectivity of the products. Experimental and computational studies reveal the reasons behind the ligand-controlled regiodivergence.

CHINESE JOURNAL OF CHEMISTRY (2022)

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Palladium-Catalyzed Nucleophilic Reaction of Alkylidenecyclopropanes with β,γ-Unsaturated α-Ketoesters: Ligand-Controlled Divergent Synthesis

Xin-Lian Liu et al.

Summary: In this study, a palladium-catalyzed ligand-controlled selective addition and cycloaddition reaction was developed for the preparation of organic compounds.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines

Yue Wang et al.

Summary: The development of stereodivergent strategies in asymmetric synthesis is crucial for accessing the full range of stereoisomers in products with multiple stereocenters. In this study, a novel P-chirogenic ligand, YuePhos, was developed to achieve precise switching of product stereochemistry in a Pd-catalyzed asymmetric cycloaddition reaction. The method provides an efficient route for the synthesis of pyrrolidines with up to three adjacent stereocenters, with excellent enantiomeric excesses.

CHEMICAL SCIENCE (2022)

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Review Chemistry, Multidisciplinary

Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions

Jianhua Wang et al.

Summary: This review focuses on transition metal-catalyzed methodologies and applications involving the cleavage of C-C bonds in vinylcyclopropanes (VCPs) for cycloaddition and related addition reactions. It discusses the properties of activated and nonactivated VCPs, transition metal-catalyzed cycloadditions, and addition reactions, as well as challenges and potential opportunities in the field.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Metal-Free Catalyzed Cyclization of N-Methoxybenzamides to Construct Quaternary Carbon-Containing Isoindolinones

Lin-Bao Zhang et al.

Summary: A simple and efficient method for constructing valuable isoindolinones through the intramolecular cyclization of N-methoxybenzamides under metal-free conditions has been developed. The reaction features low-cost catalyst, simple operation, 100% atomic economy, and excellent regioselectivity. Detailed computational studies have clarified the mechanism and demonstrated the tolerance of various functional groups.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Synthesis of Dibenzosilepin Derivatives via 1,n-Palladium Migration Coupled with anti-Carbopalladation of Alkyne

Tomohiro Tsuda et al.

Summary: A palladium-catalyzed synthesis of new members of 5H-dibenzo-[b,f]silepins was developed, showcasing the importance and potential of developing new synthetic methods based on 1,n-metal migration processes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

Zhenjie Gan et al.

Summary: A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides is reported in this study, providing optically active spiro[dihydronaphthalene-2,3'-pyrrolidine]s with one spiro quaternary and three tertiary stereogenic centers in good yields and high ee values. This protocol demonstrates high diastereo- and enantioselectivity, broad substrate scope, and mild reaction conditions.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Multidisciplinary

Rhodium Catalyzed Regioselective C-H Allylation of Simple Arenes via C-C Bond Activation of Gem-difluorinated Cyclopropanes

Zhong-Tao Jiang et al.

Summary: A rhodium-catalyzed regioselective C-H allylation of simple arenes without directing groups is reported, using gem-difluorinated cyclopropanes as reactive allyl surrogates via C-C and C-F bond activation. The method offers good yields and high selectivity under mild conditions, enabling late-stage functionalization of complex bioactive molecules. The high turnover number of the rhodium catalyst in gram-scale experiments demonstrates the efficiency of the reaction, with preliminary success in kinetic resolution for enantio-enriched gem-difluorinated cyclopropanes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Divergent Gold Catalysis: Unlocking Molecular Diversity through Catalyst Control

Chetan C. Chintawar et al.

Summary: Gold complexes have emerged as powerful catalysts in divergent catalysis, offering unique reactivity profiles due to their tunable soft pi-acidic nature. They not only catalyze reactions of alkynes, alkenes, and allenes effectively, but also provide divergent reaction pathways over other pi-acid catalysts like Ag, Pt, Pd, Rh, Cu, In, Sc, Hg, Zn, etc. Reviews documenting such examples are sporadic, hindering the further development of this burgeoning field, thus necessitating a unified approach like Divergent Gold Catalysis (DGC) to consolidate reports and pave the way for advancement.

CHEMICAL REVIEWS (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed C-C Bond Activation/Suzuki Reaction of Methylenecyclobutanes

Xiao-Bing Chen et al.

Summary: In this study, a novel palladium-catalyzed C-C bond activation of methylenecyclobutanes followed by Suzuki cross-coupling reaction was reported, leading to the formation of multisubstituted indanes. The tandem reaction process involves intramolecular carbopalladation of double bond, beta-carbon elimination, and intermolecular trapping of the transient sigma-alkylpalladium complex with boronic acids. A new TADDOL-derived phosphoramidite ligand containing fluorine and silicon-based bulky groups was found to be efficient for C-C bond activation of methylenecyclobutanes.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Lewis-Acid-Promoted Ligand-Controlled Regiodivergent Cycloaddition of Pd-Oxyallyl with 1,3-Dienes: Reaction Development and Origins of Selectivities

Weiwei Chai et al.

Summary: This study presents a novel method for the (3+2) cycloaddition reactions of palladium-oxyallyl species with 1,3-dienes, leading to the formation of five-membered carbocycles with C-C bond formation. The research also achieved regiodivergent access to cyclopentanones and cycloheptanones by tuning the steric properties of the palladium ligand. The reaction mechanism was investigated using DFT calculation, providing insights into the regioselectivities of the cycloaddition.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Ligand-Controlled, Palladium-Catalyzed Asymmetric [4+4] and [2+4] Cycloadditions

Qiuyu Li et al.

Summary: In this study, ligand-controlled, palladium-catalyzed asymmetric [4+4] and [2+4] cycloaddition reactions of benzofuran-derived azadienes were developed. Different chiral ligands were utilized to synthesize various cyclic compounds with high enantioselectivity.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Palladium-Catalyzed Defluorinative Alkylation of gem-Difluorocyclopropanes: Switching Regioselectivity via Simple Hydrazones

Leiyang Lv et al.

Summary: A cooperative strategy has been developed to switch the reaction selectivity from beta-fluoroalkene scaffolds to alkylated alpha-fluoroalkene skeletons. Key factors include the unique reactivity of hydrazones and the assistance of a steric-embedded N-heterocyclic carbene ligand. This approach allows for efficient functionalization of various gem-difluorocyclopropanes under mild conditions, including modified pharmaceutical and biological molecules.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Oscar Pamies et al.

Summary: This review covers the evolution, mechanistic understanding, and recent advances in enantioselective Pd-catalyzed allylic substitution, decarboxylative, and oxidative allylic substitutions. The catalytic data and examples of their application are collected, along with discussions on key mechanistic aspects for high selectivity and comparison with other metals. Different nucleophiles employed and ligand types for improved results in asymmetric allylic substitutions are highlighted.

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Design of 1-Phosphanorbornene Derivatives as Chiral Organocatalysts for Enantioselective (4+2) Annulation Reactions of γ-Benzyl Allenoates

Siming Jia et al.

Summary: Two novel diastereoisomeric P-chirogenic phosphine catalysts, JiaPhos, were successfully synthesized from inexpensive starting materials in five chemical operations on a 4.16g scale. These catalysts demonstrated excellent performance in enantioselective (4 + 2) annulations, providing a diverse range of 3,3'-spirocyclic oxindoles with high efficiency and enantioselectivity.

ORGANIC LETTERS (2021)

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Ligand-Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β-Unsaturated Thioesters

Han-Jun Ai et al.

Summary: Thiocarbonylation of alkynes offers a versatile method for the synthesis of unsaturated thioesters, with the possibility of controlling the product structure by using different ligands and acid additives. This approach also demonstrates the first example of thiocarbonylation of internal alkynes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Synergistic Pd/Amine-Catalyzed Stereodivergent Hydroalkylation of 1,3-Dienes with Aldehydes: Reaction Development, Mechanism, and Stereochemical Origins

Hongfa Wang et al.

Summary: A new method for metal-hydride-catalyzed hydroalkylation of 1,3-dienes with aldehydes is described, providing access to chiral molecules with allylic stereocenters. By choosing a combination of chiral palladium and amine catalysts, highly diastereo- and enantioselective access to complementary diastereomers is achieved. The mechanism involves PdH formation and migratory insertion into the alkene, followed by C-C bond formation, with the origin of stereoselectivities investigated through distortion/interaction analysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Ligand-Controlled Regiodivergent Asymmetric [5+2] and [3+2] Annulations of Vinyl Indoloxazolidones Catalyzed by Palladium

Zhi Zhao et al.

Summary: This study presents palladium-catalyzed regiodivergent asymmetric annulations of vinyl indoloxazolidones, which can act as 1,5-carbodipoles or 1,3-carbodipoles by tuning the chiral ligands and conditions, in the assemblies with sulfamate-derived cyclic imines and even activated alkenes. A diversity of polycyclic products are generally constructed with high regio- and enantioselectivity.

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Difunctionalization of Alkenes Involving Metal Migration

Yuqiang Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Palladium-Catalyzed Synthesis of Benzophenanthrosilines by C-H/C-H Coupling through 1,4-Palladium Migration/Alkene Stereoisomerization

Tomohiro Tsuda et al.

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Diastereodivergent synthesis of enantioenriched alpha,beta-disubstituted gamma-butyrolactones via cooperative N-heterocyclic carbene and Ir catalysis

Santanu Singha et al.

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Recent Advances in the Total Synthesis of Natural Products Containing Eight-Membered Carbocycles (2009-2019)

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Desymmetrization of difluoromethylene groups by C-F bond activation

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Forging Odd-Membered Rings: Palladium-Catalyzed Asymmetric Cycloadditions of Trimethylenemethane

Barry M. Trost et al.

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Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation

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Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones

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Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles

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Stereodivergent routes in organic synthesis: carbohydrates, amino acids, alkaloids and terpenes

Carmen Najera et al.

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A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Sachin S. Ichake et al.

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P-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions

Zhenjie Gan et al.

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Ag/P-Stereogenic Phosphine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions: A Method to Optically Active Pyrrolidines

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Synthesis of 2,2,5-Trisubstituted 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

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Ligand-controlled regiodivergent -allyl palladium catalysis enables a switch between [3+2] and [3+3] cycloadditions

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Chemodivergent Palladium-Catalyzed Processes: Role of Versatile Ligands

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Transition-Metal-Catalyzed Carbonylation Reactions of Olefins and Alkynes: A Personal Account

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Mild Pd-Catalyzed Aminocarbonylation of (Hetero)Aryl Bromides with a Palladacycle Precatalyst

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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2013)

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Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki-Miyaura Cross-Coupling of Allylboronates and Aryl Halides

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Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Catalyst-Controlled Regioselective Suzuki Couplings at Both Positions of Dihaloimidazoles, Dihalooxazoles, and Dihalothiazoles

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Molybdenum(0)-Promoted Carbonylative Cyclization of o-Haloaryl- and beta-Haloalkenylimine Derivatives by Oxidative Addition of a Carbon(sp(2))-Halogen Bond: Preparation of Two Types of gamma-Lactams

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes

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Nickel-Catalyzed Direct Arylation of Azoles with Aryl Bromides

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ORGANIC LETTERS (2009)

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Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline

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Enantioselective construction of spirocyclic oxindolic Cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition

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Preparation of benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation

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Palladium-catalyzed Reppe carbonylation

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Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions

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