Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes

被引：97

作者：

Zhao, Wanxiang ^{[1
]}

Montgomery, John ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, 930 North Univ Ave, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 31期

基金：

美国国家科学基金会;

关键词：

C-H CYANATION; ASYMMETRIC-SYNTHESIS; BORYLATION/ORTHO-CYANATION; BORONIC ESTERS; PALLADIUM; HYDROBORATION; DIBORATION; COMPLEXES; MECHANISM; TERTIARY;

D O I：

10.1021/jacs.6b05216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cascade cyanation/diborylation of terminal allenes proceeds efficiently with copper catalysis using bis(pinacolato)diboron (B(2)Pin(2)) and N-cyano-N-phenyl-pmethylbenzenesulfonamide (NCTS) as reagents. Mechanistic studies suggest that the process proceeds through cyanoborylation of the substituted mu-system of the allene followed by hydroboration of the remaining mu-component. A wide array of product derivatives may be accessed through site-selective cross-couplings and N-bromosuccinimide-promoted heteroarylations as well as standard oxidative and reductive conversions of the initially obtained adducts.

引用

页码：9763 / 9766

页数：4