Functionalization of Olefinic C−H Bonds by an Aryl‐to‐Vinyl 1,4‐Nickel Migration/Reductive Coupling Sequence

Author:

Yang Jingjie1,Gui Zhuofan1,He Yuli2,Zhu Shaolin134ORCID

Affiliation:

1. State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering Nanjing University Nanjing 210093 China

2. State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry School of Pharmacy China Pharmaceutical University Nanjing 210009 China

3. School of Chemistry and Chemical Engineering Henan Normal University Xinxiang 453007 China

4. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Shanghai Jiao Tong University Shanghai 200240 China

Abstract

AbstractAn attractive approach to selective functionalization of remote C−H bonds is a metal/hydride shift/cross‐coupling reaction sequence. Complimentary to the heavily exploited 1,2‐nickel/hydride shift along an sp3 chain, a chain‐walking process, the 1,4‐nickel/hydride shift along an sp2 chain is more complex. Here we report an unprecedented aryl‐to‐vinyl 1,4‐nickel/hydride shift reaction, in which the migratory alkenylnickel species generated in situ is selectively trapped by one of various coupling partners, such as isocyanates, alkyl bromides, aryl chlorides or alkynyl bromides, allowing regio‐ and stereoselective access to trisubstituted alkenes. In contrast to the well‐reported ipso‐aryl coupling reactions, this strategy provides remote alkenyl C−H functionalized products with good yield and with excellent chemo‐, regio‐ and E/Z‐selectivity.

Funder

Key Technologies Research and Development Program

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. C(sp2)–H Hydroxylation via Catalytic 1,4-Ni Migration with N2O;Journal of the American Chemical Society;2023-08-02

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