期刊
ACS CATALYSIS
卷 9, 期 5, 页码 4382-4387出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00473
关键词
photoredox catalysis; organic photocatalyst; monofluoromethylation; radical reaction; alkene difunctionalization
资金
- JSPS (KAKENHI) [22350026, 17J07953, JP16H06038, JP18H04241]
- JST CREST [JPMJCR18R4]
- Grants-in-Aid for Scientific Research [17J07953] Funding Source: KAKEN
Monofluoromethyl (CH2F) radical can be easily generated from a sulfoximine-based precursor (CH2F-S(=O)-(=NTs)-Ph) by the action of visible-light metal-free photoredox catalysis with readily accessible 1,4-bis(diphenylamino)naphthalene. The catalyst design based on the high excitation energy (E-0,E-0) and interchromophoric conjugation features a strong reducing power and a high quantum yield of emission of the photocatalyst. In addition, their photophysical properties are preserved in various polar solvents. The present system is amenable to oxy-monofluoromethylation of alkenes with high functional-group tolerance, i.e., single-step synthesis of gamma-fluoroalcohol scaffolds from various alkenes. Applications to late-stage functionalization of potentially bioactive molecules are also shown.
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