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Ethanol as a Hydrogenating Agent: Palladium‐Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides
Author(s) -
Siva Reddy Alla,
Kumara Swamy K. C.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702277
Subject(s) - chemistry , stereoselectivity , ethanol , ammonium formate , palladium , catalysis , combinatorial chemistry , organic chemistry , acetonitrile
Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source gives Z enamides. The role of ethanol in hydrogenation was demonstrated by means deuterium labeling experiment.