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

Yanli Wang; Shizheng Zhu

doi:10.1021/ol0275670

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

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

Authors

Yanli Wang¹, Shizheng Zhu

Affiliation

¹ Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, 200032, P. R. China.

PMID: 12605505
DOI: 10.1021/ol0275670

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Rhodium / chemistry

Substances

Hydrocarbons, Fluorinated
Pyrroles
Rhodium