Journal
ACS CATALYSIS
Volume 11, Issue 1, Pages 82-87Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c04722
Keywords
C alpha-H arylation; thiobenzoic acid; photocatalysis; organocatalysis; late-stage functionalization
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Funding
- University of Shizuoka
- Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research
- BINDS) from the Japan Agency for Medical Research and Development (AMED) [JP19am0101099]
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Thiobenzoic acid (TBA) can act as a single-electron reducing agent under blue light irradiation, enabling regioselective C alpha-H arylation of benzylamines, benzyl alcohols, ethers, and dihydroimidazoles through dual-role catalysis.
Thiobenzoic acid (TBA) can serve as a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie C alpha-H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in good yield, without the need for a transition-metal photocatalyst and/or synthetically elaborated organic dyes.
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