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Fluoro‐Hydroxylation of gem ‐Difluoroalkenes: Synthesis of 18 O‐labeled α‐CF 3 Alcohols
Author(s) -
Hu Jingyu,
Yang Yide,
Lou Zhengzhao,
Ni Chuanfa,
Hu Jinbo
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800426
Subject(s) - chemistry , nucleophile , hydroxylation , acetonitrile , dimethylformamide , selectfluor , electrophile , electrophilic fluorination , reagent , organic chemistry , alcohol , medicinal chemistry , combinatorial chemistry , catalysis , solvent , enzyme
In this paper, a fluoro‐hydroxylation of gem ‐difluoroalkenes is demonstrated. This protocol uses sequential electrophilic fluorination with Selectfluor and nucleophilic hydroxylation with H 2 18 O, which can be used to prepare 18 O‐labeled α‐CF 3 alcohols from gem ‐difluorostyrenes. The reaction is typically carried out at room temperature within 4 h in good to excellent yields. Other nucleophiles (besides H 2 18 O), such as alcohols, carboxylic acid, acetonitrile and N,N ‐dimethylformamide, are also suitable for this difunctionalization of gem ‐difluoroalkenes.