Tetrahedron letters

Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles

S Kamijo, C Kanazawa, Y Yamamoto

Index: Kamijo, Shin; Kanazawa, Chikashi; Yamamoto, Yoshinori Tetrahedron Letters, 2005 , vol. 46, # 15 p. 2563 - 2566

Full Text: HTML

Citation Number: 34

Abstract

The organophosphine catalyzed reaction of activated alkynes with isocyanides produces the corresponding heteroaromatization products, pyrroles, regioselectively in good yields. The reaction proceeds most probably through the 1, 4-addition of the nucleophilic phosphine catalyst to the alkynes, followed by a [3+ 2] cycloaddition between the resulting alkenyl phosphine intermediates and a carbanion derived from the isocyanides.