325809-93-6Relevant articles and documents
A catalytic fluoride-rebound mechanism for C(sp3)-CF3 bond formation
Levin, Mark D.,Chen, Tiffany Q.,Neubig, Megan E.,Hong, Cynthia M.,Theulier, Cyril A.,Kobylianskii, Ilia J.,Janabi, Mustafa,O'Neil, James P.,Toste, F. Dean
, p. 1272 - 1275 (2017)
The biological properties of trifluoromethyl compounds have led to their ubiquity in pharmaceuticals, yet their chemical properties have made their preparation a substantial challenge, necessitating innovative chemical solutions. We report the serendipitous discovery of a borane-catalyzed formal C(sp3)-CF3 reductive elimination from Au(III) that accesses these compounds by a distinct mechanism proceeding via fluoride abstraction, migratory insertion, and C-F reductive elimination to achieve a net C-C bond construction. The parent bis(trifluoromethyl)Au(III) complexes tolerate a surprising breadth of synthetic protocols, enabling the synthesis of complex organic derivatives without cleavage of the Au-C bond. This feature, combined with the fluoride-rebound mechanism, was translated into a protocol for the synthesis of 18F-radiolabeled aliphatic CF3-containing compounds, enabling the preparation of potential tracers for use in positron emission tomography.
C-Si bond cleavage of trihalomethyltrimethylsilane by alkoxo- and aryloxogold or -copper complexes
Usui, Yoko,Noma, Junko,Hirano, Masafumi,Komiya, Sanshiro
, p. 151 - 154 (2008/10/08)
The C-Si bond cleavage of trihalomethyltrimethylsilane Me3SiCX3 (X = F, Cl) proceeds smoothly by alkoxo- and aryloxogold(I or III) or -copper(I) complexes Au(OR)L (OR = OCH(CF3)2, OPh), L =PCy3, PPhs
