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Divergent Synthesis of Multisubstituted Unsymmetric Pyrroles and Pyrrolin‐4‐ones from Enamino Esters via Copper‐Catalyzed Aerobic Dimerization
Author(s) -
Chen ZhiWei,
Zheng Lei,
Liu Jin
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.201900341
Subject(s) - chemistry , trifluoroacetic acid , pyrrole , combinatorial chemistry , copper , catalysis , aryl , organic chemistry , reaction conditions , alkyl
A facile synthetic method to access multisubstituted unsymmetric pyrrole and pyrrolin‐4‐one derivatives is disclosed. In the presence of Cu(OAc) 2 and KOAc, substituted pyrrole derivatives are produced in good yields (up to 93 %) through oxidative cyclization of enamino esters. Meanwhile, using CuCl 2 and TFA (trifluoroacetic acid), pyrrolin‐4‐one derivatives are obtained in excellent yields (up to 94 %) through 1,2‐aryl migration. A wide range of functional groups have been tolerated, and a reliable method for the synthesis of valuable multisubstituted pyrroles and pyrrolin‐4‐ones has been developed.