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Copper‐Mediated Difunctionalization of Alkenylboronic Acids: Synthesis of ɑ‐Imino Ketones
Author(s) -
Jiao JiWen,
Bi HongYan,
Zou PeiSen,
Wang ZhiXin,
Liang Cui,
Mo DongLiang
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800718
Subject(s) - chemistry , enamine , copper , homolysis , imine , organic chemistry , medicinal chemistry , radical , catalysis
Various ɑ‐imino ketones were prepared in good yields through a copper‐mediated difunctionalization of alkenylboronic acids with benzotriazolamine in air. Mechanistic studies showed that ɑ‐imino ketones formation occurred through an initial copper‐mediated coupling reaction to form an enamine, followed by homolysis of the C−Cu bond to produce an ɑ‐radical imine, and finally radical oxidation by air. The ɑ‐imino ketones were easily converted to various useful scaffolds through further transformations.