One-Pot Synthesis of Butadiyne-Bridged Bipyrrole Derivatives and Bisporphyrin

Abstract

Butadiyne-bridged bipyrroles were prepared from 2-iodopyrroles and trimethylsilylacetylene through a facile one-pot synthesis involving a modified Sonogashira coupling reaction and in situ aerobic oxidative coupling of the acetylenic pyrroles; the products were obtained in yields of 31–72 % depending on the substituents on the pyrrole. The acetylene-bridged diacids obtained from the hydrolysis of the corresponding ester derivatives are highly stable, unlike most reported oligopyrrolic diacids. This protocol could be easily extended towards the synthesis of butadiyne-bridged bisporphyrins.