Premium
One‐Pot Synthesis of Butadiyne‐Bridged Bipyrrole Derivatives and Bisporphyrin
Author(s) -
Kishore M. V. Nanda,
Panda Pradeepta K.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700891
Subject(s) - chemistry , sonogashira coupling , diacetylene , acetylene , one pot synthesis , pyrrole , oxidative coupling of methane , polymer chemistry , hydrolysis , combinatorial chemistry , organic chemistry , catalysis , palladium , polymerization , polymer
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.