Direct C–H difluoromethylation of heterocycles via organic photoredox catalysis

Wei Zhang, Xin-Xin Xiang, Junyi Chen, Chen Yang, Yu-Liang Pan, Jin-Pei Cheng, Qingbin Meng () and Xin Li ()
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Wei Zhang: Nankai University
Xin-Xin Xiang: Nankai University
Junyi Chen: Beijing Institute of Pharmacology and Toxicology
Chen Yang: Nankai University
Yu-Liang Pan: Nankai University
Jin-Pei Cheng: Nankai University
Qingbin Meng: Beijing Institute of Pharmacology and Toxicology
Xin Li: Nankai University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract The discovery of modern medicine relies on the sustainable development of synthetic methodologies to meet the needs associated with drug molecular design. Heterocycles containing difluoromethyl groups are an emerging but scarcely investigated class of organofluoro molecules with potential applications in pharmaceutical, agricultural and material science. Herein, we developed an organophotocatalytic direct difluoromethylation of heterocycles using O2 as a green oxidant. The C–H oxidative difluoromethylation obviates the need for pre-functionalization of the substrates, metals and additives. The operationally straightforward method enriches the efficient synthesis of many difluoromethylated heterocycles in moderate to excellent yields. The direct difluoromethylation of pharmaceutical moleculars demonstrates the practicability of this methodology to late-stage drug development. Moreover, 2′-deoxy-5-difluoromethyluridine (F2TDR) exhibits promising activity against some cancer cell lines, indicating that the difluoromethylation methodology might provide assistance for drug discovery.

Date: 2020
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DOI: 10.1038/s41467-020-14494-8

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