RuHCl(CO)(PPh3)3-Catalyzed α-Alkylation of Ketones with Primary Alcohols

被引：118

作者：

Kuwahara, Takashi ^{[1
]}

Fukuyama, Takahide ^{[1
]}

Ryu, Ilhyong ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 18期

关键词：

TRANSFER-HYDROGENATION; ALDEHYDES; CATALYST; NANOPALLADIUM; 1,3-DIKETONES; DIMERIZATION; PROGRESS; ENONES; SYSTEM; ALDOL;

D O I：

10.1021/ol302145a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alpha-alkylation reaction of ketones with primary alcohols to give alpha-alkylated ketones was achieved using RuHCl(CO)(PPh3)(3) as a catalyst in the presence of Cs2CO3 as a base. This reaction proceeds via an aldol condensation of ketones with aldehydes, formed via transfer dehydrogenation of alcohols, to give alpha,beta-unsaturated ketones, which then undergo transfer hydrogenation with primary alcohols to give alpha-alkylated ketones and aldehydes, the latter of which participate in the next catalytic cycle. While the reaction of aliphatic primary alcohols was sluggish compared with that of benzylic alcohols, a catalytic amount of 1,10-phenanthroline was found to promote the alkylation dramatically.

引用

页码：4703 / 4705

页数：3

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