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Chem Commun (Camb). 2019 Jul 4;55(52):7446-7449. doi: 10.1039/c9cc03487k. Epub 2019 Jun 5.

Facile difluoromethylation of aliphatic alcohols with an S-(difluoro-methyl)sulfonium salt: reaction, scope and mechanistic study.

Author information

1
School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Ave., Shenzhen 518060, China. gkliu@szu.edu.cn.
2
Department of Chemistry, the Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.
3
Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

Abstract

A 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.

PMID:
31165809
DOI:
10.1039/c9cc03487k

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