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Oxidant‐Controlled Divergent Syntheses of Pyrazoles and Pyrroles by Copper(I)‐Catalyzed Oxidative Coupling of β‐Enamino Esters
Author(s) -
Jang Su San,
Chang Jun Yeong,
Kang Gil Yeong,
Youn So Won
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900351
Subject(s) - chemistry , enamine , reagent , catalysis , substrate (aquarium) , copper , oxidative coupling of methane , oxidative phosphorylation , electron transfer , combinatorial chemistry , coupling (piping) , organic chemistry , photochemistry , mechanical engineering , biochemistry , oceanography , engineering , geology
Copper(I)‐catalyzed oxidative annulations of β‐enamino esters with oxidant dependence are disclosed. These reactions offer divergent syntheses of fully substituted pyrazoles and pyrroles from a common enamine substrate through sequential C−C and N−N or C−N bond‐forming reactions in the presence of nitriles as reagent or cosolvent. A mechanism involving radical intermediates generated by single‐electron transfer (SET) is proposed for both processes.