Direct Electrochemical Defluorinative Carboxylation of gem-Difluoroalkenes with Carbon Dioxide

Shi Liang Xie; Xiao Tong Gao; Hai Hong Wu; Feng Zhou; Jian Zhou

doi:10.1021/acs.orglett.0c03051

Direct Electrochemical Defluorinative Carboxylation of gem-Difluoroalkenes with Carbon Dioxide

Shi Liang Xie
, Xiao Tong Gao
, Hai Hong Wu^*
, Feng Zhou^*
, Jian Zhou

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

We report a facile and economical synthesis of α-fluoroacrylic acids via direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2. By using a platinum plate as the working cathode and a cheap nickel plate as the anode in a user-friendly undivided cell under constant current conditions, the reactions proceed smoothly under room temperature, without the use of expensive transition metal catalysts, ligands, external base or reductant, affording the desired adducts in up to 83% yield and 20:1 Z/E ratio, with good functional group tolerance. A cyclic voltammetry study was conducted and suggested a novel ECEC process.

Original language	English
Pages (from-to)	8424-8429
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.0c03051
State	Published - 6 Nov 2020

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title = "Direct Electrochemical Defluorinative Carboxylation of gem-Difluoroalkenes with Carbon Dioxide",

abstract = "We report a facile and economical synthesis of α-fluoroacrylic acids via direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2. By using a platinum plate as the working cathode and a cheap nickel plate as the anode in a user-friendly undivided cell under constant current conditions, the reactions proceed smoothly under room temperature, without the use of expensive transition metal catalysts, ligands, external base or reductant, affording the desired adducts in up to 83\% yield and 20:1 Z/E ratio, with good functional group tolerance. A cyclic voltammetry study was conducted and suggested a novel ECEC process.",

author = "Xie, \{Shi Liang\} and Gao, \{Xiao Tong\} and Wu, \{Hai Hong\} and Feng Zhou and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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day = "6",

doi = "10.1021/acs.orglett.0c03051",

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T1 - Direct Electrochemical Defluorinative Carboxylation of gem-Difluoroalkenes with Carbon Dioxide

AU - Xie, Shi Liang

AU - Gao, Xiao Tong

AU - Wu, Hai Hong

AU - Zhou, Feng

AU - Zhou, Jian

PY - 2020/11/6

Y1 - 2020/11/6

N2 - We report a facile and economical synthesis of α-fluoroacrylic acids via direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2. By using a platinum plate as the working cathode and a cheap nickel plate as the anode in a user-friendly undivided cell under constant current conditions, the reactions proceed smoothly under room temperature, without the use of expensive transition metal catalysts, ligands, external base or reductant, affording the desired adducts in up to 83% yield and 20:1 Z/E ratio, with good functional group tolerance. A cyclic voltammetry study was conducted and suggested a novel ECEC process.

AB - We report a facile and economical synthesis of α-fluoroacrylic acids via direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with CO2. By using a platinum plate as the working cathode and a cheap nickel plate as the anode in a user-friendly undivided cell under constant current conditions, the reactions proceed smoothly under room temperature, without the use of expensive transition metal catalysts, ligands, external base or reductant, affording the desired adducts in up to 83% yield and 20:1 Z/E ratio, with good functional group tolerance. A cyclic voltammetry study was conducted and suggested a novel ECEC process.

UR - https://www.scopus.com/pages/publications/85094643790

U2 - 10.1021/acs.orglett.0c03051

DO - 10.1021/acs.orglett.0c03051

M3 - 文章

C2 - 33044834

AN - SCOPUS:85094643790

SN - 1523-7060

VL - 22

SP - 8424

EP - 8429

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Direct Electrochemical Defluorinative Carboxylation of gem-Difluoroalkenes with Carbon Dioxide

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