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

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 % dependin...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-09, Vol.2017 (35), p.5197-5203
Main Authors: Kishore, M. V. Nanda, Panda, Pradeepta K.
Format: Article
Language:English
Subjects:
Acetylene
Alkynes
Biaryls
Chemical synthesis
Coupling
Cross–coupling
C–C coupling
Derivatives
Porphyrinoids
Pyrroles
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Summary: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. Butadiyne‐bridged bipyrroles are obtained from the corresponding iodopyrroles through a one‐pot strategy, which is subsequently applied to the synthesis of butadiyne‐bridged bisporphyrin in good yield. DBU = 1,8‐diazabicyclo[5.4.0]undec‐7‐ene, TMSA = trimethylsilylacetylene.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700891