||Palladium-Catalyzed Zinc-Amide-Mediated C[BOND]H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides.
Otsuka, Shinya ,
Yorimitsu, HidekiOsuka, Atsuhiro
Chemistry - A European Journal
14707 , 2015-10-12 , wiley
Article first published online: 31 JUL 2015
C[BOND]H arylation of polyfluoroarenes and heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium–N-heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl⋅LiCl, plays a key role as an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding aryl halides. Aryl sulfides that are prepared through sulfur-specific reactions, such as SNAr sulfanylation and extended Pummerer reactions, undergo this direct arylation, offering interesting transformations that are otherwise difficult to achieve with conventional halogen-based organic synthesis.