101048-46-8Relevant articles and documents
Radical Trifluoroacetylation of Alkenes Triggered by a Visible-Light-Promoted C–O Bond Fragmentation of Trifluoroacetic Anhydride
Jeschke, Gunnar,Katayev, Dmitry,N?tel, Nicolas Yannick,Rombach, David,Zhang, Kun
supporting information, p. 22487 - 22495 (2021/09/09)
We report a mild and operationally simple trifluoroacylation strategy of olefines, that utilizes trifluoroacetic anhydride as a low-cost and readily available reagent. This light-mediated process is fundamentally different from conventional methodologies and occurs through a trifluoroacyl radical mechanism promoted by a photocatalyst, which triggers a C?O bond fragmentation. Mechanistic studies (kinetic isotope effects, spectroelectrochemistry, optical spectroscopy, theoretical investigations) highlight the evidence of a fleeting CF3CO radical under photoredox conditions. The trifluoroacyl radical can be stabilized under CO atmosphere, delivering the trifluoroacetylation product with higher chemical efficiency. Furthermore, the method can be turned into a trifluoromethylation protocol by simply changing the reaction parameters. Beyond simple alkenes, this method allows for chemo- and regioselective functionalization of small-molecule drugs and common pharmacophores.
A Weinreb amide approach to the synthesis of trifluoromethylketones
Rudzinski, Diandra M.,Kelly, Christopher B.,Leadbeater, Nicholas E.
supporting information, p. 9610 - 9612 (2012/10/29)
A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.
Reaction of 1,2-unsaturated trifluoromethyl ketones and their conversion to 1-(trifluoromethyl)furan derivatives
Zhang, Dehui,Yuan, Chengye
, p. 3916 - 3924 (2008/02/13)
A novel synthetic approach leading to 1-(trifluoromethyl)furan derivatives is reported. 4-Aryl-1,1,1-trifluorobut-3-en-2-one was iodinated and subsequently reduced to give the corresponding alcohol. The resultant iodo compound was then subjected to coupli