Ruthenium-Catalyzed Selective Hydrogenation of Epoxides to Secondary Alcohols

被引：30
|
作者：
Thiyagarajan, Subramanian [1 ]
Gunanathan, Chidambaram [1 ]
机构：
[1] HBNI, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Odisha, India
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 23期
关键词：
LITHIUM ALUMINUM-HYDRIDE; TERMINAL EPOXIDES; CHEMOSELECTIVE HYDROGENOLYSIS; REGIOSELECTIVE REDUCTION; OXIDATION; HYDROSILYLATION; ISOMERIZATION; OLEFINS; SYSTEM; ACID;
D O I：
10.1021/acs.orglett.9b03995
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ruthenium(II)-catalyzed highly selective Markovnikov hydrogenation of terminal epoxides to secondary alcohols is reported. Diverse substitutions on the aryl ring of styrene oxides are tolerated. Benzylic, glycidyl, and aliphatic epoxides as well as diepoxides also underwent facile hydrogenation to provide secondary alcohols with exclusive selectivity. Metal-ligand cooperation-mediated ruthenium trans-dihydride formation and its reaction involving oxygen and the less substituted terminal carbon of the epoxide is envisaged for the origin of the observed selectivity.
引用
收藏
页码：9774 / 9778
页数：5
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