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One‐Pot Controlled Reduction of Conjugated Amides by Sequential Double Hydrosilylation Catalyzed by an Iridium(III) Metallacycle
Author(s) -
Corre Yann,
Rysak Vincent,
Nagyházi Márton,
Kalocsai Dorottya,
Trivelli Xavier,
Djukic JeanPierre,
AgbossouNiedercorn Francine,
Michon Christophe
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001061
Subject(s) - hydrosilylation , metallacycle , iridium , conjugated system , silylation , catalysis , chemistry , ketene , cationic polymerization , combinatorial chemistry , aminal , organic chemistry , polymer chemistry , medicinal chemistry , polymer , physics , x ray crystallography , diffraction , optics
A single and accessible cationic iridium III metallacycle effectively catalyzes the one‐pot sequential double hydrosilylation of challenging α,β‐unsaturated secondary and tertiary amides to afford, in a controlled and straightforward way, the corresponding reduced products, namely, the related secondary and tertiary amides and amines. The catalytic hydrosilylations of the conjugated amides described herein proceeded in good yields and high chemoselectivities. The critical silyl enolate, in other words silyl ketene aminal intermediate, has been observed and characterized by using control experiments, mass spectrometry and state of the art NMR analyses. The present achievements indicate a promising potential of catalysts based on metallacycles for future significant developments in one‐pot multicatalytic synthesis and therefore the production of highly functionalized and complex organic molecules.