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A Copper‐Catalyzed Synthesis of Pyrroles through Photochemically Generated Acylazirines
Author(s) -
Paternoga Jan,
Opatz Till
Publication year - 2019
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.201901176
Subject(s) - chemistry , isomerization , catalysis , copper , photochemistry , valence (chemistry) , dual role , combinatorial chemistry , metal , organic chemistry
A synthesis of highly substituted 2,4‐diacylpyrroles through a Cu‐catalyzed dimerization of acylazirines generated in situ by a photochemical valence isomerization is described. The shown methodology allows the use of simple precursors and a readily available copper(II)‐catalyst. Since the reaction is best performed at elevated temperatures, a method to adjust the temperature of the reaction mixture during this dual light and metal‐induced process was established. Additionally, mechanistic studies of the reaction were performed in order to provide a deeper understanding of the chemistry of 2‐acylazirines.