Electrooxidation-induced arylsulfonylation of xanthene derivatives with DABSO as an SO2 surrogate DOI
Yi Pan, Zhenjie Qi, Wenxue Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An electrochemical redox C(sp3)-H arylsulfonylation of xanthenes has been developed using aryl diazonium tetrafluoroborates and DABSO as the arylsulfone source. This radical reaction proceeds via formation arylsulfonyl radicals from between DABSO, followed by a cross-coupling process. Notably, occurs in absence any catalyst or external oxidant, providing efficient sulfonylation with broad functional group compatibility.

Language: Английский

Recent advances in electrochemical oxidative cross-coupling with hydrogen evolution involving radicals DOI
Yong Yuan, Jie Yang, Aiwen Lei

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(18), P. 10058 - 10086

Published: Jan. 1, 2021

This tutorial review provides an overview of the most recent developments in electrochemical oxidative cross-coupling with hydrogen evolution involving radicals.

Language: Английский

Citations

350

Cross-dehydrogenative coupling: a sustainable reaction for C–C bond formations DOI
Tian Tian, Zhiping Li, Chao‐Jun Li

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(18), P. 6789 - 6862

Published: Jan. 1, 2021

We provide a review of the progress cross-dehydrogenative coupling reactions in constructing wide variety C–C bonds. Sustainable can be combined with multiple forms energy output.

Language: Английский

Citations

196

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(19), P. 11269 - 11335

Published: Sept. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Language: Английский

Citations

148

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update DOI
Monica Oliva, Guglielmo Coppola, Erik V. Van der Eycken

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(7), P. 1810 - 1834

Published: Feb. 16, 2021

Abstract Transition metal‐catalysed processes have been widely used for the functionalization of inert C−H bonds. Strategies benzylic position having a relatively weak bond (bond dissociation energy∼ 80–90 kcal/mol) differ from aliphatic and aromatic positions with stronger The recent advances in direct activation through generation C( sp 3 ) radicals demonstrated potential electrochemistry photochemistry as means constructing new chemical This review will cover progress organic radical strategies employing sustainable tools. In addition, mechanistic details typical reactions included which, turn, help researchers to look at this promising area different perspective towards discoveries often hidden opportunities. magnified image

Language: Английский

Citations

112

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds DOI

Qinhui Wan,

Zhongyi Zhang,

Zhong‐Wei Hou

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2830 - 2848

Published: Jan. 1, 2023

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds and their mechanistic insights synthetic applications have been summarized.

Language: Английский

Citations

80

Electrochemical oxidative C(sp3)–H cross-coupling with hydrogen evolution DOI

Zhaoliang Yang,

Wenyan Shi, Hesham Alhumade

et al.

Nature Synthesis, Journal Year: 2023, Volume and Issue: 2(3), P. 217 - 230

Published: Feb. 16, 2023

Language: Английский

Citations

68

Recent advances in the radical-mediated decyanative alkylation of cyano(hetero)arene DOI Creative Commons

Shiqi Tong,

Kewei Li, Xuan‐Hui Ouyang

et al.

Green Synthesis and Catalysis, Journal Year: 2021, Volume and Issue: 2(2), P. 145 - 155

Published: April 19, 2021

Substituted pyridines are very important skeleton in natural products, agrochemicals and pharmaceuticals, which not only can be used to synthesis chiral ligands functional materials but also as building blocks the construction of new photo- or electrochemical properties. As a result, much efforts have been developed towards such compounds. Given great influence these methodologies organic chemistry, we summarize recent progress radical-mediated decyanative alkylation reactions cyano(hetero)arene via photo/electrochemistry radical pathway, C(sp3)-H, C(sp2)-H, C–C C-hetero bonds cleavaged bond is formed. We discussed mechanisms reactions.

Language: Английский

Citations

87

Electrochemical Benzylic C–H Functionalization with Isocyanides DOI
Shanyu Tang, Régis Guillot, Laurence Grimaud

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2125 - 2130

Published: March 14, 2022

We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)–H bonds with an isocyanide via electrochemical process giving rise to structures that are encountered in several biologically relevant compounds and drugs. This transformation proceeds under mild conditions without need for any external oxidant avoids necessity start from a prefunctionalized substrate deployment cation pool method. The anodic oxidation position subsequent addition lead formation C–C bond nitrilium hydrolyzes yield α-aryl acetamide derivatives, whereas elimination t-butyl delivers acetonitrile derivatives.

Language: Английский

Citations

28

Electrochemical benzylic C–H arylation of xanthenes and thioxanthenes without a catalyst and oxidant DOI
Hui Gao, Xinyu Chen, Pei-Long Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(7), P. 1911 - 1916

Published: Jan. 1, 2022

A catalyst-free and oxidant-free C–H arylation of xanthenes thioxanthenes using electrochemistry has been developed, which affords a number cross-coupling products in moderate to good yields.

Language: Английский

Citations

26

Electrochemical oxidative cascade cyclization of olefinic amides and alcohols leading to the synthesis of alkoxylated 4H-3,1-benzoxazines and indolines DOI

Wan‐Jie Wei,

Lei Zhan,

Caina Jiang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(3), P. 928 - 933

Published: Jan. 1, 2023

We have developed a mild and efficient electrochemical oxidative strategy to construct anticancer alkoxylated 4 H -3,1-benzoxazines indolines without the requirement for transition-metal catalyst an external oxidant.

Language: Английский

Citations

16