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Transition metal catalyzed regioselective carbon-carbon bond formation mediated by transfer hydrogenation

One of the more formidable challenges in the synthesis of complex organic molecules remains the efficient formation of carbon-carbon bonds. The development of a broad class of reactions to achieve this goal involves the addition of carbon based nucleophiles to carbonyl and imine compounds. Until recently, classical approaches to carbon-carbon bond formation generally required the use of stoichiometric pre-formed organometallic reagents to serve as nucleophiles, which translate into stoichiometric organometallic byproducts. In an effort to minimize nucleophile pre-activation and byproduct formation, our lab has developed efficient methods for carbonyl and imine additions via in situ formation of alkyl metal nucleophiles from π-unsaturates. The research reported herein describes our advances in an assortment of transition metal-catalyzed carbon-carbon bond forming reactions mediated by transfer hydrogenation, including regioselective hydrohydroxymethylation, hydrohydroxyfluoroalkylation, and hydroaminomethylation. Additionally, the investigation of regioselective carbonyl vinylation is reported. / text

Identiferoai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/30512
Date03 September 2015
CreatorsSam, Brannon
ContributorsKrische, Michael J.
Source SetsUniversity of Texas
LanguageEnglish
Detected LanguageEnglish
TypeThesis
Formatapplication/pdf

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