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Synthesis of Secondary Enamides by Ruthenium‐Catalyzed Selective Addition of Amides to Terminal Alkynes
Author(s) -
Gooßen Lukas J.,
Salih Kifah S. M.,
Blanchot Mathieu
Publication year - 2008
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.200803068
Subject(s) - ruthenium , isomerization , trifluoromethanesulfonate , catalysis , chemistry , combinatorial chemistry , terminal (telecommunication) , markovnikov's rule , organic chemistry , regioselectivity , computer science , telecommunications
Enamides made easy : A catalyst system generated in situ using bis(2‐methallyl)(cycloocta‐1,5‐diene)ruthenium(II), 1,4‐bis(dicyclohexylphosphino)butane, and ytterbium triflate efficiently catalyzes the addition of primary amides to terminal alkynes, selectively forming the Z ‐anti‐Markovnikov enamides. The E isomers are also accessible by combining the hydroamidation with an in situ double‐bond isomerization reaction.