506437-44-1Relevant articles and documents
Catalytic Domino Reaction of Ketones/Aldehydes with Me3SiCF2Br for the Synthesis of α-Fluoroenones/α-Fluoroenals
Song, Xiaoning,Chang, Jian,Zhu, Dongsheng,Li, Jiaheng,Xu, Cong,Liu, Qun,Wang, Mang
supporting information, p. 1712 - 1715 (2015/04/14)
A unique domino reaction of enolizable carbonyl compounds with Me3SiCF2Br to construct α-fluoroenones and α-fluoroenals is described to undergo the in situ formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination sequence. In this tandem reaction, Me3SiCF2Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. It allows the transformations to occur smoothly under only a catalytic amount of n-Bu4NBr as initiator.
Palladium-catalyzed carbonylative coupling of tributyl(1-fluorovinyl)stannane with aryl halides and aryl triflates
Hanamoto, Takeshi,Handa, Kumiko,Mido, Tomonori
, p. 2497 - 2502 (2007/10/03)
We have found that tributyl(1-fluorovinyl)stannane (2) could be readily prepared from the reaction of (1-fluorovinyl)methyldiphenylsilane1 (1) and bis(tributyltin) oxide in the presence of a catalytic amount of CsF in DMF in good yields. The palladium-catalyzed carbonylative cross-coupling reaction of 2 with aryl iodides bearing various functional groups smoothly proceeded giving the corresponding aryl 1-fluorovinyl ketones in good yields under an atmospheric pressure of carbon monoxide. A similar carbonylative cross-coupling reaction of 2 with aryl triflates was also accomplished in the presence of tetrabutylammonium iodide (Bu4NI) as an additive.
