Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols

被引:22
|
作者
Paudel, Keshav [1 ,2 ]
Xu, Shi [1 ]
Ding, Keying [1 ,2 ]
机构
[1] Middle Tennessee State Univ, Dept Chem, Murfreesboro, TN 37132 USA
[2] Middle Tennessee State Univ, Mol Biosci Program, Murfreesboro, TN 37132 USA
基金
美国国家科学基金会;
关键词
ALPHA; BETA-UNSATURATED NITRILES; HYDROGENATION; DEHYDROGENATION; ACETONITRILE; CYANATION; AMINES; EARTH;
D O I
10.1021/acs.orglett.1c01553
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first switchable alpha-olefination and alpha-alkylation of nitriles with primary alcohols catalyzed by a well-defined base transition-metal Co complex was presented. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding products by this method. It is noteworthy that the transformation is environmentally benign and atom efficient with H-2 and H2O being the sole byproducts.
引用
收藏
页码:5028 / 5032
页数:5
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