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Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents
Author(s) -
Bower John F.,
Kim In Su,
Patman Ryan L.,
Krische Michael J.
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.200802938
Subject(s) - reagent , aldehyde , catalysis , chemistry , stoichiometry , transfer hydrogenation , metal , metal carbonyl , surface modification , alcohol , organic chemistry , alcohol oxidation , combinatorial chemistry , organic synthesis , ruthenium
Abstract Classical protocols for carbonyl allylation, propargylation and vinylation typically rely upon the use of preformed allyl metal, allenyl metal and vinyl metal reagents, respectively, mandating stoichiometric generation of metallic byproducts. Through transfer hydrogenative CC coupling, however, carbonyl addition may be achieved from the aldehyde or alcohol oxidation level in the absence of stoichiometric organometallic reagents or metallic reductants. Here, we review transfer hydrogenative methods for carbonyl addition, which encompass the first catalytic protocols enabling direct CH functionalization of alcohols.