Palladium-catalyzed coupling of polyfluorinated arenes with heteroarenes via C-F/C-H activation.

Org Lett

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.

Published: February 2013

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Article Abstract

The first palladium-catalyzed coupling of 2-pyridyl-polyfluoroarenes and benzoxazole, thiazole, benzothiazole, benzoimidazole, oxazole or oxadiazole via a concurrent C-F/C-H activation is described. Initial mechanistic studies showed that C-F activation of perfluoroarene is likely the rate-limiting step of the catalytic cycle. This protocol provides a useful and operationally simple process to functionalized polyfluoroarenes.

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http://dx.doi.org/10.1021/ol303567tDOI Listing

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