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Copper‐Catalyzed Difunctionalization of Terminal Alkynes with Diazo Esters and Amines to Construct β‐Enamino Esters
Author(s) -
Gao Bao,
Huang Hanmin
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600883
Subject(s) - chemistry , diazo , yield (engineering) , tandem , catalysis , combinatorial chemistry , copper , amino esters , reaction conditions , terminal (telecommunication) , organic chemistry , materials science , metallurgy , composite material , telecommunications , computer science
An operationally simple and efficient copper‐catalyzed three‐component tandem reaction of terminal alkynes, diazo compounds and amines to yield β‐enamino esters is described. This straightforward protocol takes place rapidly with a wide range of substrates and gives the desired β‐enamino esters in good to excellent yields. Preliminary mechanistic studies suggested that the reaction probably proceeds through Cu‐catalyzed formal C–H insertion to produce an alkynoate intermediate, which was then trapped by amines to give the β‐enamino esters.