Pairing Electrocarboxylation of Unsaturated Bonds with Oxidative Transformation of Alcohol and Amine

Xin Zhang; Zonghan Li; Hongshuai Chen; Chaoren Shen; Haihong Wu; Kaiwu Dong

doi:10.1002/cssc.202300807

Pairing Electrocarboxylation of Unsaturated Bonds with Oxidative Transformation of Alcohol and Amine

Xin Zhang
, Zonghan Li
, Hongshuai Chen
, Chaoren Shen
, Haihong Wu^*
, Kaiwu Dong^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

10 Scopus citations

Abstract

A parallel paired electrosynthetic method, coupling electrocarboxylation incorporating CO₂ into ketone, imine, and alkene with alcohol oxidation or oxidative cyanation of amine, was developed for the first time. Various carboxylic acids as well as aldehyde/ketone or α-nitrile amine were prepared at the cathode and anode respectively in a divided cell. Its utility and merits on simultaneously achieving high atom-economic CO₂ utilization, elevated faradaic efficiency (FE, total FE of up to 166 %), and broad substrate scope were demonstrated. The preparation of pharmaceutical intermediates for Naproxen and Ibuprofen via this approach proved its potential application in green organic electrosynthesis.

Original language	English
Article number	e202300807
Journal	ChemSusChem
Volume	16
Issue number	19
DOIs	https://doi.org/10.1002/cssc.202300807
State	Published - 6 Oct 2023

Keywords

alcohol oxidation
carbon dioxide
carboxylation
cyanation
paired electrolysis

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title = "Pairing Electrocarboxylation of Unsaturated Bonds with Oxidative Transformation of Alcohol and Amine",

abstract = "A parallel paired electrosynthetic method, coupling electrocarboxylation incorporating CO2 into ketone, imine, and alkene with alcohol oxidation or oxidative cyanation of amine, was developed for the first time. Various carboxylic acids as well as aldehyde/ketone or α-nitrile amine were prepared at the cathode and anode respectively in a divided cell. Its utility and merits on simultaneously achieving high atom-economic CO2 utilization, elevated faradaic efficiency (FE, total FE of up to 166 \%), and broad substrate scope were demonstrated. The preparation of pharmaceutical intermediates for Naproxen and Ibuprofen via this approach proved its potential application in green organic electrosynthesis.",

keywords = "alcohol oxidation, carbon dioxide, carboxylation, cyanation, paired electrolysis",

author = "Xin Zhang and Zonghan Li and Hongshuai Chen and Chaoren Shen and Haihong Wu and Kaiwu Dong",

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TY - JOUR

T1 - Pairing Electrocarboxylation of Unsaturated Bonds with Oxidative Transformation of Alcohol and Amine

AU - Zhang, Xin

AU - Li, Zonghan

AU - Chen, Hongshuai

AU - Shen, Chaoren

AU - Wu, Haihong

AU - Dong, Kaiwu

PY - 2023/10/6

Y1 - 2023/10/6

N2 - A parallel paired electrosynthetic method, coupling electrocarboxylation incorporating CO2 into ketone, imine, and alkene with alcohol oxidation or oxidative cyanation of amine, was developed for the first time. Various carboxylic acids as well as aldehyde/ketone or α-nitrile amine were prepared at the cathode and anode respectively in a divided cell. Its utility and merits on simultaneously achieving high atom-economic CO2 utilization, elevated faradaic efficiency (FE, total FE of up to 166 %), and broad substrate scope were demonstrated. The preparation of pharmaceutical intermediates for Naproxen and Ibuprofen via this approach proved its potential application in green organic electrosynthesis.

AB - A parallel paired electrosynthetic method, coupling electrocarboxylation incorporating CO2 into ketone, imine, and alkene with alcohol oxidation or oxidative cyanation of amine, was developed for the first time. Various carboxylic acids as well as aldehyde/ketone or α-nitrile amine were prepared at the cathode and anode respectively in a divided cell. Its utility and merits on simultaneously achieving high atom-economic CO2 utilization, elevated faradaic efficiency (FE, total FE of up to 166 %), and broad substrate scope were demonstrated. The preparation of pharmaceutical intermediates for Naproxen and Ibuprofen via this approach proved its potential application in green organic electrosynthesis.

KW - alcohol oxidation

KW - carbon dioxide

KW - carboxylation

KW - cyanation

KW - paired electrolysis

UR - https://www.scopus.com/pages/publications/85166225401

U2 - 10.1002/cssc.202300807

DO - 10.1002/cssc.202300807

M3 - 文章

C2 - 37366066

AN - SCOPUS:85166225401

SN - 1864-5631

VL - 16

JO - ChemSusChem

JF - ChemSusChem

IS - 19

M1 - e202300807

ER -

Pairing Electrocarboxylation of Unsaturated Bonds with Oxidative Transformation of Alcohol and Amine

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