Electrochemical Benzylic C–H Carboxylation DOI

Wei-Mei Zeng,

Chunhui Peng,

Youai Qiu

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 9, 2025

Direct benzylic C-H carboxylation stands as a high atom economy, efficient, and convenient route for the synthesis of valuable carboxylic acids, which are great significance in many pharmaceuticals bioactive molecules. However, inherent inertness both bonds carbon dioxide presents challenge further transformations. Herein, we report our efforts to overcome this obstacle via halide-promoted linear paired electrolysis generate various acids. Remarkably, process is transition-metal- base-free, making it environmentally benign cost-effective. Besides, suitable constructing wide range primary, secondary, tertiary acids under mild reaction conditions, demonstrating broad substrate scopes good functional group tolerance. Furthermore, protocol enables direct some drug molecules, including Flurbiprofen, Ibuprofen, Naproxen, facilitates late-stage modification complex compounds, showcasing practical application synthetic chemistry underscores its potential advance related compounds.

Language: Английский

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
Recent Advances in Reactions Involving Carbon Dioxide Radical Anion DOI
Wei Xiao, Jun Zhang, Jie Wu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(24), P. 15991 - 16011

Published: Nov. 28, 2023

Carbon dioxide radical anion (CO2•–) is a highly reactive nucleophilic species that has recently emerged in organic chemistry as strong single electron donor (reductant) and reactant for the synthesis of carboxylic acids. In general, CO2•– can be generated by either direct reduction CO2 or HAT formate salts. Achievements reactions involving have been witnessed recent years. This Review summarizes advances highlighting some challenges identifying potential areas improvement, which may offer inspiration future studies.

Language: Английский

Citations

58
Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 450 - 470

Published: Nov. 3, 2023

Language: Английский

Citations

50
Organo‐Mediator Enabled Electrochemical Deuteration of Styrenes DOI

Keming Yang,

Tian Feng, Youai Qiu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(45)

Published: Sept. 12, 2023

Despite widespread use of the deuterium isotope effect, selective labeling chemical molecules remains a major challenge. Herein, facile and general electrochemically driven, organic mediator enabled deuteration styrenes with oxide (D2 O) as economical source was reported. Importantly, this transformation could be suitable for various electron rich mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition-metal catalysts, affording desired products in good yields excellent D-incorporation (D-inc, up to >99 %). Mechanistic investigations means experiments cyclic voltammetry tests provided sufficient support transformation. Notably, method proved powerful tool late-stage biorelevant compounds.

Language: Английский

Citations

49
Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls DOI

Maorui Wang,

Chengqian Zhang, Chenggang Ci

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(20), P. 10967 - 10973

Published: April 19, 2023

Despite the widespread applications of α-hydroxyalkyl cyclic amines, direct and diverse access to such a class unique vicinal amino alcohols still remains, date, challenge. Here, through strategy electroreductive α-hydroxyalkylation inactive N-heteroarenes with ketones or electron-rich arylaldehydes, we describe room temperature approach for construction which features broad substrate scope, operational simplicity, high chemoselectivity, no need pressurized H2 gas transition metal catalysts. The zinc ion generated from anode oxidation plays crucial role in activation both reactants by decreasing their reduction potentials. electroreduction combination Lewis acids this work is anticipated develop more useful transformations.

Language: Английский

Citations

47
Recent Advances in Electrochemical Carboxylation with CO2 DOI

Guo‐Quan Sun,

Li‐Li Liao,

Chuan‐Kun Ran

et al.

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: 57(18), P. 2728 - 2745

Published: Sept. 3, 2024

ConspectusCarbon dioxide (CO

Citations

36
Visible-light-driven synthesis of N-heteroaromatic carboxylic acids by thiolate-catalysed carboxylation of C(sp²)–H bonds using CO2 DOI
Yuan‐Xu Jiang, Li‐Li Liao, Tianyu Gao

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(3), P. 394 - 405

Published: Jan. 11, 2024

Language: Английский

Citations

26
Electroreduction of unactivated alkenes using water as hydrogen source DOI Creative Commons
Yanwei Wang, Qian Wang, Lei Wu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: March 30, 2024

Abstract Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination anodic iron salts and silane generated in situ via cathodic reduction, using H 2 O as H-source. The catalytic amounts Si-additive work H-carrier from to generate a highly active species under continuous electrochemical conditions. This approach shows broad substrate scope good functional group compatibility. In addition hydrogenation, use D instead provides desired deuterated products yields with excellent D-incorporation (up >99%). Further late-stage hydrogenation complex molecules drug derivatives demonstrate potential application pharmaceutical industry. Mechanistic studies are performed provide support for proposed mechanistic pathway.

Language: Английский

Citations

22
Recent Advances in Photochemical/Electrochemical Carboxylation of Olefins with CO2 DOI
Qian Wang, Yanwei Wang, Min Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2249 - 2266

Published: May 15, 2024

Comprehensive Summary CO 2 is an abundant, nontoxic, and renewable C1 feedstock in synthetic chemistry. Direct carboxylation of readily available olefins incorporating regarded as a promising strategy to access high value‐added carboxylic acids well fixation. However, due the thermodynamic stability kinetic inertness difficulty controlling regioselectivity, with still remains challenging. Radical‐type functionalization represented powerful protocol enabled development novel transformations this realm. More recently, advance new technology, such photoredox catalysis renaissance electrochemistry organic synthesis, offered unique chemical reactivities radical precursors provided solutions olefins. This review presents recent advances radical‐type olefins, which has mainly been achieved through photocatalysis electrocatalysis last decade. In article, we provide comprehensive introduction progress, summarize advantages limitations current research, discuss potential outlook for further development. Key Scientists

Language: Английский

Citations

19
Electrocatalytic three-component reactions: synthesis of tellurium-containing oxazolidinone for anticancer agents DOI

Xue‐Qi Zhou,

Haitao Tang, Fei‐Hu Cui

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(13), P. 5024 - 5029

Published: Jan. 1, 2023

A new synthetic method involving electrochemical catalysis were used to synthesize various tellurium-containing oxazolidinones which showed better antitumor activity compared other oxazolidinones.

Language: Английский

Citations

44