Palladium-Catalyzed Oxidative Cross-Coupling Reaction of Arylboronic Acids with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates

被引:70
|
作者
Tsoi, Yuk-Tai
Zhou, Zhongyuan
Chan, Albert S. C.
Yu, Wing-Yiu [1 ]
机构
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chiosci, Kowloon, Hong Kong, Peoples R China
关键词
ALPHA-DIAZOCARBONYL COMPOUNDS; CARBENE INSERTION; BIOLOGICAL EVALUATION; ARYLATION;
D O I
10.1021/ol101796t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed oxidative cross-coupling reaction of arylboronic acids with alpha-diazoesters was achieved using molecular oxygen as the sole reoxidant, and E-alpha,beta-diarylacrylates were obtained in good yields and >20 1 E-to-Z selectivity
引用
收藏
页码:4506 / 4509
页数:4
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