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Palladium‐Catalyzed Addition of 1,3‐Diones to Ynamides: An Entry to Alkoxy‐Substituted Enamides
Author(s) -
Graux Lionel V.,
Clavier Hervé,
Buono Gérard
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.201402398
Subject(s) - catalysis , chemistry , alkoxy group , cationic polymerization , palladium , lewis acids and bases , combinatorial chemistry , metal , medicinal chemistry , stereochemistry , organic chemistry , alkyl
Abstract A new metal‐catalyzed addition reaction of 1,3‐diketones to ynamides, which provides access to unprecedented alkoxy‐substituted enamides, is disclosed herein. A screening of catalytic systems showed that both a phosphapalladacycle and a cationic gold complex were capable of promoting this reaction rapidly and cleanly. The scope investigation revealed that variously substituted terminal ynamides and cyclic 1,3‐diones were well tolerated. The use of internal ynamides led to the formation of both E and Z isomers with low to good selectivities. The proposed mechanism suggests that the phosphapalladacycle acts as a π Lewis acid to activate the ynamide.