Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3

被引：184

作者：

Orita, A ^{[1
]}

Tanahashi, C ^{[1
]}

Kakuda, A ^{[1
]}

Otera, J ^{[1
]}

机构：

[1] Okayama Univ Sci, Okayama 7000005, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 26期

关键词：

D O I：

10.1021/jo0107453

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bi(OTf)(3)-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)(3)/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable methyl ester realized quite easy separation of the desired acylation product. The Bi(OTf)(3)/acid anhydride protocol was applicable to a wide spectrum of alcohols bearing various functionalities. Acid-labile THP- or TBS-protected alcohol, furfuryl alcohol, and geraniol could be acylated as well as base-labile alcohols. Even acylation of functionalized tertiary alcohols was effected at room temperature.

引用

页码：8926 / 8934

页数：9

共 45 条

[31] Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis [J].