Organocatalytic Methods for Chemoselective O-tert-Butoxycarbonylation of Phenols and Their Regeneration from the O-t-Boc Derivatives

被引：27

作者：

Chankeshwara, Sunay V. ^{[1
]}

Chebolu, Rajesh ^{[1
]}

Chakraborti, Asit K. ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Sas Nagar 160062, Punjab, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 21期

关键词：

D O I：

10.1021/jo8013325

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbon tetrabromide (CBr4) catalyzes O-tert-butoxycarbonylation of functionalized phenols without any side reactions (bromination, addition of CBr3 to a double bond, and formation of symmetrical diaryl carbonates, cyclic carbonates. or carbonic-carbonic anhydrides). The parent phenols are regenerated from the O-t-Boc derivatives by the catalyst system CBr4-PPh3 without affecting other protecting groups (aryl alkyl ether, alkyl ester, and thioacetal) or competitive side reaction such as bromination, nitrene (from NO2) and alpha,alpha-dibromoolefine (with CHO/COMe)formation, and transesterification (with CO2Me/Et) taking place.

引用

页码：8615 / 8618

页数：4

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