Facile difluoromethylation of aliphatic alcohols with an S-(difluoro-methyl)sulfonium salt: reaction, scope and mechanistic study
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AbstractA facile and practical approach for the difluoromethylation of aliphatic alcohols with an S-(difluoromethyl)sulfonium salt was developed. A wide variety of alcohols with broad functional groups are compatible to furnish the corresponding alkyl difluoromethyl ethers in good to excellent yields under mild reaction conditions. Control experiments and DFT computational studies suggest that the difluoromethylation of alcohols mainly proceeds via a difluorocarbene pathway involving a five-membered transition state with the participation of water, whose crucial role in this reaction was also elucidated by control experiments.
Acceptance Date28/05/2019
All Author(s) ListG.-K. Liu, X. Li, W.-B. Qin, X.-S. Peng, H.N.C. Wong, L. Zhang, X. Zhang
Journal nameChemical Communications
Year2019
Month7
Day4
Volume Number55
Issue Number52
PublisherRoyal Society of Chemistry
Place of PublicationUnited Kingdom
Pages7446 - 7449
ISSN1359-7345
LanguagesEnglish-United Kingdom
Keywordsdifluoromethylation, S-(difluoromethyl)sulfonium salt, aliphatic alcohol, mechanistic study

Last updated on 2020-03-07 at 03:21