Synthetic scope of Ru(OH)x/Al2O3-catalyzed hydrogen-transfer reactions:: An application to reduction of allylic alcohols by a sequential process of isomerization/meerwein-ponndorf-verley-type reduction

被引：46

作者：

Kim, Jung Won ^{[1
]}

Koike, Takeshi ^{[1
]}

Kotani, Miyuki ^{[2
]}

Yamaguchi, Kazuya ^{[1
,2
]}

Mizuno, Noritaka ^{[1
,2
]}

机构：

[1] Univ Tokyo, Sch Engn, Dept Appl Chem, Bunkyo Ku, Tokyo 1138656, Japan

[2] Japan Sci & Technol Agcy, CREST, Kawaguchi, Saitama 3320012, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 13期

关键词：

allylic compounds; heterogeneous catalysis; reaction mechanisms; reduction; ruthenium;

D O I：

10.1002/chem.200701917

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reduction of allylic alcohols can be promoted efficiently by the supported ruthenium catalyst Ru(OH)(x)/ Al2O3. Various allylic alcohols were converted to saturated alcohols in excellent yields by using 2-propanol without any additives. This Ru(OH)(x)/ Al2O3-catalyzed reduction of a dienol proceeds only at the allylic double bond to afford the corresponding enol, and chemoselective isomerization and reduction can be realized under similar conditions. The catalysis is truly heterogeneous and the high catalytic performance can be maintained during at least three recycles of the Ru(OH)(x)/ Al2O3 catalyst. The transformation of allylic alcohols to saturated alcohols consists of three sequential reactions: oxidation of allylic alcohols to a,p-unsaturated carbonyl compounds; reduction of a,p-unsaturated carbonyl compounds to saturated carbonyl compounds; and reduction of saturated carbonyl compounds to saturated alcohols.

引用

页码：4104 / 4109

页数：6

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