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PPh 3 ‐Catalyzed Reactions of Alkyl Propiolates with N ‐Tosylimines: A Facile Synthesis of Alkyl 2‐[aryl(tosylimino)methyl]acrylate and an Insight into the Reaction Mechanism
Author(s) -
Liu Huimin,
Zhang QiongMei,
Wang Limin,
Tong Xiaofeng
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902105
Subject(s) - zwitterion , chemistry , alkyl , aryl , catalysis , enamine , phosphonium , methyl acrylate , deuterium , catalytic cycle , acrylate , reaction mechanism , medicinal chemistry , combinatorial chemistry , organic chemistry , copolymer , molecule , polymer , physics , quantum mechanics
A new PPh 3 ‐catalyzed synthesis of alkyl 2‐[aryl(tosylimino)methyl]acrylates from propiolate and N ‐tosylimine has been developed. Deuterium‐labelling experiments show that the reaction mechanism involves several hydrogen‐transfer processes, which are not the turnover‐limiting step and strongly rely on the nature of the reaction media. The stable phosphonium–enamine zwitterion, which was proven to play an important role in the catalytic cycle, has been isolated and characterised by X‐ray analysis.