期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 44, 页码 23827-23834出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202110257
关键词
alkynes; hypervalent iodine; photochemistry; quaternary centers; synthetic methods
资金
- ERC (European Research Council, Starting Grant iTools4MC) [334840]
- EPFL
- Swiss National Science Foundation
- Ecole Polytechnique Federale de Lausanne
- European Research Council (ERC) [334840] Funding Source: European Research Council (ERC)
In this study, aryl-substituted ethynylbenziodoxolone reagents were found to be directly activated by visible light irradiation, acting as oxidants and radical traps in various EBX-mediated processes. This eliminates the need for a photocatalyst, simplifying the reaction conditions.
Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C-H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.
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