期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 4, 页码 1262-1265出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504838
关键词
alcohols; fluorine; homogeneous catalysis; iridium; photochemistry
资金
- JSPS [26288045, 15K13689, 15J12072]
- Naito Foundation
- Grants-in-Aid for Scientific Research [15J12072, 15K13689, 26288045] Funding Source: KAKEN
We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis. The use of fac-[Ir(ppy)3] (ppy=2-pyridylphenyl) photocatalyst and shelf-stable Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, as a CF2H source is the key to success. The well-designed photoredox system achieves synthesis of not only beta-CF2H-substituted alcohols but also ethers and an ester from alkenes through solvolytic processes. The present method allows a single-step and regioselective formation of C(sp(3))-CF2H and C(sp(3))-O bonds from C=C moiety in alkenes, such as hydroxydifluoromethylation, regardless of terminal or internal alkenes. Moreover, this methodology tolerates a variety of functional groups.
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