Yu, You-Jie; Zhang, Feng-Lian; Peng, Tian-Yu; Wang, Chang-Ling; Cheng, Jie; Chen, Chen; Houk, Kendall N.; Wang, Yi-Feng published their research in Science (Washington, DC, United States) in 2021. The article was titled 《Sequential C-F bond functionalizations of trifluoroacetamides and acetates via spin-center shifts》.Electric Literature of C19H18BrP The article contains the following contents:
Defluorinative functionalization of readily accessible trifluoromethyl groups constitutes an economical route to partially fluorinated mols. However, the controllable replacement of one or two fluorine atoms while maintaining high chemoselectivity remains a formidable challenge. Here we describe a general strategy for sequential carbon-fluorine (C-F) bond functionalizations of trifluoroacetamides and trifluoroacetates. The reaction begins with the activation of a carbonyl oxygen atom by a 4-dimethylaminopyridine-boryl radical, followed by a spin-center shift to trigger the C-F bond scission. A chemoselectivity-controllable two-stage process enables sequential generation of difluoro- and monofluoroalkyl radicals, which are selectively functionalized with different radical traps to afford diverse fluorinated products. The reaction mechanism and the origin of chemoselectivity were established by exptl. and computational approaches. After reading the article, we found that the author used Methyltriphenylphosphonium bromide(cas: 1779-49-3Electric Literature of C19H18BrP)
Methyltriphenylphosphonium bromide(cas: 1779-49-3) is an organophosphorus compound, with potential use as a precursor and a solvent in organic synthesis. And it is used widely for methylenation via the Wittig reaction.Electric Literature of C19H18BrP
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary