Iridium-Catalyzed C-H Borylation of Cyclopropanes

被引：126
|
作者：
Liskey, Carl W.
Hartwig, John F. [1 ]
机构：
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 09期
基金：
美国国家科学基金会;
关键词：
REGIOSPECIFIC FUNCTIONALIZATION; N-CYCLOPROPYLATION; ARYL; REAGENTS; AMIDES; ARENES; BONDS; ALKYL;
D O I：
10.1021/ja400103p
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The borylation of cyclopropanes catalyzed by the combination of (eta(6)-mes)IrBpin(3) or [Ir(COD)-OMe](2) and a phenanthroline derivative is reported. The borylation occurs selectively at the methylene C-H bonds of the cyclopropane ring over methine or methyl C-H bonds. High diasteroselectivities were observed from reactions catalyzed by the combination of iridium and 2,9-Me(2)phenanthroline. The cyclopropylboronate esters that are generated are versatile synthetic intermediates that can be converted to trifluoroborate salts, boronic acids, cyclopropylarenes, cyclopropylamines, and cyclopropanols.
引用
收藏
页码：3375 / 3378
页数：4
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