Journal
NATURE COMMUNICATIONS
Volume 10, Issue -, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/s41467-019-12844-9
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Funding
- National Natural Science Foundation of China [21971108, 21971111, 21702098, 21732003, 21672099]
- Natural Science Foundation of Jiangsu Province [BK20190006]
- Fundamental Research Funds for the Central Universities [020514380176]
- Jiangsu Six Peak Talent Project
- 1000-Youth Talents Plan
- Nanjing University
- Scientific Research Foundation of Graduate School of Nanjing University [2018CL05]
- innovation experiment program for undergraduates of Jiangsu province
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The benzylic positions in drugs are sites that readily react with cytochrome P450 oxidases via single-electron oxidation. New synthetic methodologies to incorporate a fluoroalkyl group at the benzylic site are continually being developed, and in this paper, we report a metal-free and site-selective organophotoredox-catalyzed trifluoromethylthiolation of benzylic C-H bonds for a wide variety of alkyl arenes and heteroarenes. The precise and predictive regioselectivity among various C(sp(3))-H bonds originates from an inner-sphere benzylic radical initiation mechanism, and avoids the use of external oxidants or hydrogen atom abstractors. Its practicality stems from the trifluoromethylthiolation of a series of drugs and complex organic molecules, which is overwhelmingly selective for benzyl groups. This operationally simple protocol can provide a general and practical access to structurally diverse benzylic trifluoromethyl sulfides produced from ubiquitous benzylic C-H bonds. Large scale trifluoromethylthiolation can be achieved with continuous flow photoredox technology.
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