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. 2019 Feb 14;10(11):3181-3185.
doi: 10.1039/c9sc00100j. eCollection 2019 Mar 21.

Electrochemical fluoromethylation triggered lactonizations of alkenes under semi-aqueous conditions

Sheng Zhang  1 , Lijun Li  1 , Jinjin Zhang  1 , Junqi Zhang  1 , Mengyu Xue  1 , Kun Xu  1   2
Affiliations

Electrochemical fluoromethylation triggered lactonizations of alkenes under semi-aqueous conditions

Sheng Zhang et al. Chem Sci. .

Abstract

An electrochemical difluoromethylation triggered lactonization of alkenes was developed for the first time. This protocol employs readily prepared CF2HSO2Na as the difluoromethylating reagent, affording unprecedented CF2H-containing lactones in moderate yields. Moreover, with CF3SO2Na as the trifluoromethylating reagent, a wide array of CF3-containing lactones were obtained under additional supporting electrolyte- and catalyst-free conditions.

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Figures

Scheme 1
Scheme 1. Electrochemical difluoromethylations.
Fig. 1
Fig. 1. Cyclic voltammograms of substrates in 0.1 M LiClO4/CH3CN, using a Pt wire working electrode and glassy carbon and Ag/AgNO3 (0.1 M in CH3CN) as counter and reference electrodes at a 100 mV s–1 scan rate: (a) background (0.1 M LiClO4 in CH3CN), (b) CF3SO2Na (5 mmol L–1), (c) CF2HSO2Na (5 mmol L–1), and (d) 1a (5 mmol L–1).
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