Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds
Fan Yu1, Wengui Wang1, Shoufeng Wang1
1Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, People's Republic of China.
Abstract:
An efficient copper-catalyzed selective fluoromethylthiolation of an inert δ-C(sp3)-H bond in sulfonamides was reported. In the presence of a copper catalyst and PhSO2SRf, the radical generated through 1,5-hydrogen atom transfer (HAT) was sufficiently trapped by PhSO2SRf, instead of copper, which was prevalent in metal-catalyzed radical-relay processes, incorporating a fluoromethylthio group into molecules. The general substrate scope and mild conditions endowed the method with wide potential applications in pharmaceuticals and agrochemicals.
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