Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts

Angewandte Chemie
Chuan Liu, Qiu Wang

Abstract

α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C-H zincation and copper-catalyzed C(sp3 )-C(sp2 ) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.

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Citations

Jul 7, 2019·Angewandte Chemie·Jie ChenTeck-Peng Loh
Feb 18, 2021·Organic Letters·Chao-Shen ZhangXiang-Yu Chen
Aug 28, 2019·Organic Letters·Konrad KepskiWesley J Moran
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Dec 13, 2018·Organic Letters·Liangliang Zhang, Martin Oestreich
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Nov 20, 2018·Journal of the American Chemical Society·Shao-Zhen NieVy M Dong
Apr 15, 2020·Organic Letters·Yuichiro WatanabeMasanobu Uchiyama
Oct 29, 2021·The Journal of Organic Chemistry·Yue ShiXu Zhang

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