4.5 Review

Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Nickel-Catalyzed Intramolecular Alkene Difunctionalization by Ball-Milling

Matthew T. J. Williams et al.

Summary: A mechanochemical nickel-catalyzed intramolecular difunctionalization reaction of alkene tethered aryl halides with alkyl halides is developed for the synthesis of 3,3-disubstituted heterocycles, namely oxindoles, with shorter reaction times compared to solution-phase methods. The process is solvent minimized by employing liquid-assisted grinding (LAG) quantities of DMA and avoids the need for chemical activation of the terminal reductant (manganese) through mechanical grinding. The reaction can be scaled up to yield gram quantities of product and modest enantioinduction is possible with a chiral PyrOx ligand.

ADVANCED SYNTHESIS & CATALYSIS (2023)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Diarylation of Internal Acyclic Styrenes and Enamides

Yang Xi et al.

Summary: This study reports a new catalyst system for the enantioselective transformation of internal acyclic alkenes. By applying different reaction types to two common acyclic alkenes, products with asymmetric centers were obtained. Moreover, the formation of incontiguous stereocenters was achieved through an interrupted chain-walking process.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Three-Component Asymmetric Ni-Catalyzed 1,2-Dicarbofunctionalization of Unactivated Alkenes via Stereoselective Migratory Insertion

Omar Apolinar et al.

Summary: An asymmetric 1,2-dicarbofunctionalization of unactivated alkenes with aryl iodides and aryl/alkenylboronic esters under nickel/bioxazoline catalysis is reported. The reaction exhibits a wide substrate scope and affords the products with high yield and enantioselectivity. In addition to terminal alkenes, 1,2-disubstituted internal alkenes can also participate in the reaction, resulting in the formation of two contiguous stereocenters with high diastereoselectivity and moderate enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Multidisciplinary Sciences

Enantioselective nickel-catalyzed dicarbofunctionalization of 3,3,3-trifluoropropene

Yun-Ze Li et al.

Summary: The authors report a nickel-catalyzed enantioselective dicarbofunctionalization reaction of 3,3,3-trifluoropropene, which overcomes side reactions and provides a convenient method for the synthesis of chiral trifluoromethylated compounds.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Physical

Synthesis of tri- and tetrasubstituted stereocentres by nickel-catalysed enantioselective olefin cross-couplings

Chen-Fei Liu et al.

Summary: Asymmetric transition-metal catalysis has a significant impact on chemical synthesis, but non-precious metal-catalysed strategies for enantioenriched compounds with multiple stereogenic centers are rare. This study presents a sterically encumbered chiral N-heterocyclic carbene-Ni(O) catalyst, combined with an organotriflate and a metal alkoxide as hydride donor, to promote 1,2-hydroarylation and hydroalkenylation reactions of various alkenes and 1,3-dienes.

NATURE CATALYSIS (2022)

Article Chemistry, Multidisciplinary

Enantioselective Three-Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates

Shenghan Teng et al.

Summary: Asymmetric coupling efficiently occurs between propargylic acetates, cycloalkenes, and electron-rich heteroarenes, yielding 2,3-disubstituted tetrahydrofurans and pyrrolidines in trans configuration with excellent enantiomeric ratios. The reaction proceeds via Wacker-type attack of nucleophilic heteroarenes on alkenes activated by allenyl Pd-II species.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Pei Fan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization

Justin Diccianni et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling

Hai-Yong Tu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes

Youxiang Jin et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Carbamoyl Fluoride-Enabled Enantioselective Ni-Catalyzed Carbocarbamoylation of Unactivated Alkenes

Yue Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Nickel-catalyzed enantioselective reductive carbo-acylation of alkenes

Yun Lan et al.

COMMUNICATIONS CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes

Youxiang Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes

Zhi-Xiong Tian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Physical

Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes

Teng Ma et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

Matteo Chierchia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Three-component vicinal-diarylation of alkenes via direct transmetalation of arylboronic acids

Yun Zhang et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

Kuai Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Multidisciplinary Sciences

Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement

Liang Zhang et al.

SCIENCE (2016)

Article Chemistry, Multidisciplinary

Synthesis of Diversely Functionalized Oxindoles Enabled by Migratory Insertion of Isocyanide to a Transient σ-Alkylpalladium(II) Complex

Wangqing Kong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel

Ji-Wei Gu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles

Huan Cong et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)