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Nickel‐Catalyzed Heck‐Type Alkenylation of Secondary and Tertiary α‐Carbonyl Alkyl Bromides
Author(s) -
Liu Chao,
Tang Shan,
Liu Dong,
Yuan Jiwen,
Zheng Liwei,
Meng Lingkui,
Lei Aiwen
Publication year - 2012
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.201108350
Subject(s) - alkyl , catalysis , quaternary carbon , chemistry , carbonyl group , nickel , organic chemistry , catalytic cycle , medicinal chemistry , enantioselective synthesis
Ni made it! A novel Heck‐type reaction of secondary and tertiary α‐carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1‐diaryl alkenes were utilized as substrates to easily construct α‐alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving Ni I /Ni II is proposed based on our experimental results. EWG=electron‐withdrawing group.