Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls

作者：Senaweera Sameera; Weaver Jimmie D

来源：Journal of the American Chemical Society, 2016, 138(8): 2520-2523.

DOI：10.1021/jacs.5b13450

Multifluorinated biaryls are challenging to synthesize and yet are an important class of molecules. Because of the difficulty associated with selective fluorination, this class of molecules represent a formidable synthetic challenge. An alternative approach to selective fluorination of biaryls is to couple an arene that already possesses C-F bonds in the desired location. This strategy has been regularly utilized and relies heavily on traditional cross-coupling strategies that employ organometallics and halides (or pseudohalides) in order to achieve the coupling. Herein we report conditions for the photocatalytic coupling via direct functionalization of the C-F bond of a perfluoroarene and C-H bond of the other arene to provide an expedient route to multifluorinated biaryls. The mild conditions and good functional group tolerance enable a broad scope, including access to the anti-Minisci product of basic heterocycles. Finally, we demonstrate the value of the C-F functionalization approach by utilizing the high fluorine content to systematically build complex biaryls containing between two and five Caryl-F bonds via the synergistic use of photocatalysis and SNAr chemistry.

• 出版日期2016-3-2