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Synthesis 2023; 55(18): 2843-2859
DOI: 10.1055/a-2036-2074
short review
Special Issue Electrochemical Organic Synthesis

Electrochemical Difunctionalization of Alkenes

Jing-Hao Qin∗
a   State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
b   Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
,
Ning Nan
a   State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
b   Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
,
Jin-Heng Li∗
a   State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. of China
b   Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
c   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
d   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China
› Author AffiliationsWe thank the National Natural Science Foundation of China (Nos 21871126 and 22271245) and the Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University (No. 2021ZD01) and Jiangxi Province Science and Technology Project (No. 20224BAB213014) for financial support.
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Abstract

The electrochemical alkene difunctionalization reaction has become a powerful and sustainable tool for the efficient construction of vicinal difunctionalized structures in organic synthesis. Since only electrons are used as the redox agents, electrochemical alkene difunctionalization avoids the need for additional redox catalysts, metal catalysts, or chemical oxidants and does not generate chemical waste. Herein we summarize the latest contributions in the electrochemical difunctionalization of alkenes over the last 3–4 years. We discuss in detail the reaction features, scope, limitations, and mechanistic rationalizations of three categories of alkene difunctionalization methods: (1) electrochemical alkene difunctionalization terminated by nucleophiles, (2) electrochemical difunctionalization of alkenes terminated by radicals, and (3) electrochemical alkene difunctionalization terminated by functionality migration.

1 Introduction

2 Electrochemical Alkene Difunctionalization Terminated by Nucleophiles

2.1 Sulfonylative Difunctionalization of Alkenes

2.2 Sulfurizative/Sulfoxidative Difunctionalization of Alkenes

2.3 Azidotetrazolation of Alkenes

2.4 Trifluoromethylative Difunctionalization of Alkenes

2.5 Diarylation of Alkenes

3 Electrochemical Difunctionalization of Alkenes Terminated by Radicals

3.1 Direct Radical-Coupling-Enabled Alkene Difunctionalization

3.2 Metal-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization

3.3 Metalloid-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization

4 Electrochemical Alkene Difunctionalization Terminated by Functionality Migration

5 Summary and Outlook

Key words

electrochemistry - alkene difunctionalization - radical - radical transfer coupling - functionality migration


Publication History

Received: 07 January 2023

Accepted after revision: 15 February 2023

Accepted Manuscript online:
15 February 2023

Article published online:
13 March 2023

© 2023. Thieme. All rights reserved

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