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Silver‐Catalyzed Functionalization of Esters by Carbene Transfer: The Role of Ylide Zwitterionic Intermediates
Author(s) -
Gava Riccardo,
Fuentes M. Ángeles,
Besora Maria,
Belderrain Tomás R.,
Jacob Kane,
Maseras Feliu,
Etienne Michel,
Caballero Ana,
Pérez Pedro J.
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402241
Subject(s) - carbene , ylide , diazo , chemistry , catalysis , ethyl diazoacetate , context (archaeology) , surface modification , acetone , photochemistry , cyclopropanation , transfer hydrogenation , organic chemistry , combinatorial chemistry , medicinal chemistry , ruthenium , paleontology , biology
The reaction of esters with ethyl diazoacetate catalyzed by the complex [F 27 –Tp 4 Bo,3 CF 2 CF 3Ag(acetone)] generates α‐(acyloxy)acetates in moderate to high yields. This is a novel transformation in the context of carbene‐transfer reactions from diazo compounds that, according to experimental and theoretical data, is suggested to occur through zwitterionic intermediates.