Journal
CHEMCATCHEM
Volume 13, Issue 12, Pages 2952-2958Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.202100304
Keywords
photocatalysis; radical reactions; alkenes; fluorine; cyclization
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Funding
- Basic Research Programs of Yunnan Province [2018FH001-002, 2019FGF01/2019-1-C-25318000002188]
- National Natural Science Foundation of China [22061024]
- Yunnan Ten Thousand Talent Program for Young Top-Notch Talents
- Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province
- Undergraduate Education Reform Project of Yunnan Universities [JG2018172]
- Kunming University
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This study presents a complementary oxidative photocatalytic strategy for the cyclizative aryltrifluoromethylations of alkenes and CF3SO2Na. The protocol is general and functional-group tolerant, offering a variety of CF3-containing heterocycles. Extensive mechanistic investigations revealed the role of p-nitroanisole in enhancing proton photoreduction via proton-coupled electron transfer.
A complementary oxidative photocatalytic strategy is presented. In the presence of 4-nitroanisole, hexafluoroisopropanol (HFIP) as a proton source is activated and the proton photoreduction is enhanced, enabling a range of cyclizative aryltrifluoromethylations of alkenes and CF3SO2Na (Langlois' reagent) with hydrogen evolution. Such a protocol is general, for both activated and unactivated olefins could be used as the substrates, affording a variety of CF3-containing heterocycles such as indolines, indolin-2-ones, 3,4-dihydroisoquinolin-1-ones, 5,6-dihydrobenzoimidazo[2,1-a]isoquinolines, benzoimidazo[2,1-a]isoquinolin-6(5H)-ones and 1,2,3,4-tetrahydroisoquinolines, under mild and metal- and oxidant-free conditions with a good functional-group tolerance. Extensive mechanistic investigations revealed that p-nitroanisole (p-NA) does not react with the photocatalyst directly as an oxidant, but rather activates HFIP via proton-coupled electron transfer (PCET) and scavenges some of the reduced protons to improve proton photoreduction.
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