Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 38, Pages 13318-13322Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201906381
Keywords
C-H functionalization; Electrophotocatalysis; oxidation; radical dication; trisaminocyclopropenium ion
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Funding
- National Institutes of Health [R35 GM127135]
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC001944]
- National Science Foundation [DGE-16-44869]
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Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C-H/N-H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
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