title: Copper-Catalyzed Reaction of Trifluoromethylketones with Aldehydes via a Copper Difluoroenolate.
abstract: A copper-catalyzed reaction of easily accessible α,α,α-trifluoromethylketones with various aldehydes affords difluoro-methylene compounds in the presence of diboron and NaOtBu. The key process of the reaction is the formation of a copper difluoroenolate by 1,2-addition of a borylcopper intermediate to α,α,α-trifluoromethylketones and subsequent β-fluoride elimination. Mechanistic studies including the isolation and characterization of a possible anionic copper alkoxide intermediate are also described.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan) http://www.chem.eng.osaka-u.ac.jp/∼ogoshi-lab/en/index.html.
authors.forename: Ryohei
authors.initials: R
authors.lastname: Doi
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan) http://www.chem.eng.osaka-u.ac.jp/∼ogoshi-lab/en/index.html.
authors.forename: Masato
authors.initials: M
authors.lastname: Ohashi
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan) http://www.chem.eng.osaka-u.ac.jp/∼ogoshi-lab/en/index.html. ogoshi@chem.eng.osaka-u.ac.jp.
authors.forename: Sensuke
authors.initials: S
authors.lastname: Ogoshi
keywords: CF activation; aldol reaction; boron; copper; synthetic methods