通过铑（II）催化的分子内N-H插入反应便捷合成多官能化β-氟吡咯

Convenient synthesis of polyfunctionalized beta-fluoropyrroles from rhodium(II)-catalyzed intramolecular N-H insertion reactions.

作者信息

Wang Yanli, Zhu Shizheng

机构信息

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, P. R. China.

出版信息

Org Lett. 2003 Mar 6;5(5):745-8. doi: 10.1021/ol0275670.

DOI:10.1021/ol0275670

PMID:12605505

Abstract

Polyfunctionalized beta-fluoropyrrole can be readily prepared from rhodium(II) acetate-catalyzed intramolecular N-H insertion reaction of delta-amino-gamma,gamma-difluoro-alpha-diazo-beta-ketoesters. A cyanomethylene group can be introduced at C-3 of the pyrrole ring through the Wittig reaction of the diazo compounds followed by rhodium(II)-catalyzed intramolecular N-H insertion reactions.

摘要

多官能化的β-氟代吡咯可通过醋酸铑（II）催化的δ-氨基-γ，γ-二氟-α-重氮-β-酮酯的分子内N-H插入反应轻松制备。通过重氮化合物的维蒂希反应，然后进行铑（II）催化的分子内N-H插入反应，可在吡咯环的C-3位引入一个亚甲基氰基。