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Alkenylation of C(sp 3 )−H Bonds by Zincation/Copper‐Catalyzed Cross‐Coupling with Iodonium Salts
Author(s) -
Liu Chuan,
Wang Qiu
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713278
Subject(s) - chemistry , stereospecificity , phosphine , copper , catalysis , coupling reaction , coupling (piping) , medicinal chemistry , organic chemistry , polymer chemistry , materials science , metallurgy
α‐Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C−H zincation and copper‐catalyzed C(sp 3 )−C(sp 2 ) 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.