Late-Stage Trifluoromethylthiolation of Benzylic C–H Bonds

Jin Xie and Chengjian Zhu present the photoredox-catalyzed trifluoromethylthiolation of benzylic C–H bonds.

It is estimated that over 20% of small-molecule drugs on the market contain at least one fluorine atom. The trifluoromethyl group – which is a xenobiotic function, not yet found in any naturally available compound – is also encountered in a number of drugs, generally as an aromatic substituent but sometimes connected to a heteroatom such as oxygen or sulfur. Due to its strongly electron­withdrawing characteristics and high lipophilicity, the selective introduction of the trifluoromethylthio group (SCF3) into organic and pharmaceutical molecules can improve their cell membrane permeability and metabolic stability of the target molecules. Hence, synthetic strategies for introducing an SCF3 group in organic molecules entailing versatility, diversity and availability are highly desirable in the arsenal of synthetic chemists.
In a recent paper, the group of Professors Jin Xie and Chengjian Zhu at Nanjing University (P. R. of China) developed an organophotoredox­catalyzed reaction for site­selective benzylic C–H bond trifluoromethylthiolation of a wide variety of alkyl arenes and heteroarenes.

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