Oxidative Difunctionalization of Alkenyl MIDA Boronates: A Versatile Platform for Halogenated and Trifluoromethylated α-Boryl Ketones

被引：71

作者：

Lv, Wen-Xin ^{[1
]}

Zeng, Yao-Fu ^{[1
]}

Li, Qingjiang ^{[1
,2
]}

Chen, Yunyun ^{[1
]}

Tan, Dong-Hang ^{[1
]}

Yang, Ling ^{[1
]}

Wang, Honggen ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

[2] Peking Univ, Stake Key Lab Nat & Biomimet Drugs, Beijing, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 34期

基金：

中国国家自然科学基金;

关键词：

alkenes; halogenation; organoboron; oxidation; trifluoromethylation; SMALL-MOLECULE SYNTHESIS; BUILDING-BLOCKS; SODIUM TRIFLUOROMETHANESULFINATE; CARBONYL-COMPOUNDS; AROMATIC-COMPOUNDS; ARYLBORONIC ACIDS; FACILE SYNTHESIS; CUPRIC ACETATE; EFFICIENT; INSERTION;

D O I：

10.1002/anie.201604898

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of halogenated and trifluoromethylated alpha-boryl ketones via a one-pot oxidative difunctionalization of alkenyl MIDA boronates is reported. These novel densely functionalized organoborons bearing synthetically and functionally valuable carbonyl, halogen/CF3 and boronate moieties within the same molecule are synthetically challenging for the chemist, but have great synthetic potential, as demonstrated by their applications in a straightforward synthesis of borylated furans. The generality of this reaction was extensively investigated. This reaction is attractive since the starting materials, alkenyl MIDA boronates, are easily accessible.

引用

页码：10069 / 10073

页数：5

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