Recent Advances in Electrochemical, Ni‐Catalyzed C−C Bond Formation DOI Creative Commons
Mareena C. Franke, Daniel J. Weix

Israel Journal of Chemistry, Journal Year: 2023, Volume and Issue: 64(1-2)

Published: July 27, 2023

Abstract Nickel‐catalyzed cross‐electrophile coupling (XEC) is an efficient method to form carbon‐carbon bonds and has become important tool for building complex molecules. While XEC most often used stoichiometric metal reductants, these transformations can also be driven electrochemically. Electrochemical ( e XEC) attractive because it increase the greenness of this potential resulted in numerous advances recent years. The focus review on electrochemical, Ni‐catalyzed bond forming reactions reported since 2010 categorized by type anodic half reaction: sacrificial anode, reductant, convergent paired electrolysis. key developments are highlighted need more scalable options discussed.

Language: Английский

Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides DOI Creative Commons
Dong Liu,

Zhao‐Ran Liu,

Zhenhua Wang

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Nov. 28, 2022

Electrochemical asymmetric catalysis has emerged as a sustainable and promising approach to the production of chiral compounds utilization both anode cathode working electrodes would provide unique for organic synthesis. However, precise matching rate electric potential anodic oxidation cathodic reduction make such idealized electrolysis difficult achieve. Herein, cross-coupling between α-chloroesters aryl bromides is probed model reaction, wherein alkyl radicals are generated from through sequential oxidative electron transfer process at anode, while nickel catalyst reduced lower state cathode. Radical clock studies, cyclic voltammetry analysis, paramagnetic resonance experiments support synergistic involvement redox events. This electrolytic method provides an alternative avenue that could find significant utility in

Language: Английский

Citations

68
Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis DOI
Wenzhao Zhang,

Nianmin Hong,

Song Lu

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2574 - 2584

Published: April 9, 2021

Abstract Electroorganic synthesis has recently become a rapidly blossoming research area within the organic community. It should be noted that electrochemical reaction is always balanced system with two half‐cell reactions‐oxidation and reduction. Most strategies, however, typically focus on one of sides for desired transformations. Paired electrolysis desirable half reactions running simultaneously, thus maximizing overall margin atom energy economy. Meanwhile, spatial separation between oxidation reduction essential feature electrochemistry, offering unique opportunities development redox‐neutral would otherwise challenging to accomplish in conventional flask setting. This review discusses most recent illustrative examples paired special emphasis sequential convergent processes.

Language: Английский

Citations

67
Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization DOI
Vincent Corcé, Cyril Ollivier, Louis Fensterbank

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(4), P. 1470 - 1510

Published: Jan. 1, 2022

Recent developments in the use of boron, silicon, nitrogen and sulfur derivatives single-electron transfer reactions for generation alkyl radicals are described. Photoredox catalyzed, electrochemistry promoted or thermally-induced oxidative reductive processes discussed highlighting their synthetic scope discussing mechanistic pathways.

Language: Английский

Citations

67
Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis DOI Creative Commons
Chen Zhu, Ajit Prabhakar Kale, Huifeng Yue

et al.

JACS Au, Journal Year: 2021, Volume and Issue: 1(7), P. 1057 - 1065

Published: June 15, 2021

A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well aryl tosylates can be efficiently coupled a series of N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines sulfonamides are also suitable substrates. Interestingly, when benzophenone imine applied in the arylation, product selectivity toward formation amine addressed by base switch. In addition, alternating current mode successfully applied. DFT calculations support facilitated reductive elimination pathway.

Language: Английский

Citations

64
Electrophotochemical Decarboxylative Azidation of Aliphatic Carboxylic Acids DOI
Yukang Wang, Liubo Li, Niankai Fu

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(17), P. 10661 - 10667

Published: Aug. 16, 2022

We report an electrophotochemical metal-catalyzed strategy that harnesses the power of light and electricity for radical decarboxylative functionalization aliphatic carboxylic acids. This environmentally friendly protocol smoothly converts a diverse array acids into corresponding alkyl azides without using chemical oxidants or azido-group transfer reagents. The visible energy electric can be applied in spatially separated fashion with modular electro-flow-cell large-scale synthesis.

Language: Английский

Citations

50
Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp3–sp2 Carbon–Carbon Bonds DOI Creative Commons
James L. Douthwaite, Ruheng Zhao, Eunjae Shim

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(20), P. 10930 - 10937

Published: May 15, 2023

Amines and carboxylic acids are abundant synthetic building blocks that classically united to form an amide bond. To access new pockets of chemical space, we interested in the development amine-acid coupling reactions complement coupling. In particular, formation carbon-carbon bonds by formal deamination decarboxylation would be impactful addition synthesis toolbox. Here, report a cross-coupling alkyl amines aryl C(sp

Language: Английский

Citations

30
The Multiple Roles of Bipyridine-Nickel(II) Complex in Versatile Photoredox C(sp2)–C(sp3) Cross-Coupling DOI
Jingsheng Li,

Tengfei Kang,

Xiao Yi

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3328 - 3338

Published: Feb. 9, 2025

Language: Английский

Citations

2
Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis DOI Creative Commons

Yun-Zhao Wang,

Bing Sun, Jianfeng Guo

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 28, 2025

Abstract Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling benzyl chlorides aryl halides, yielding chiral 1,1-diaryl compounds good to excellent enantioselectivity. This catalytic reaction can not only be applied chlorides/bromides, which are challenging access other means, but also containing silicon groups. Additionally, absence sacrificial anode lays foundation for scalability. The combination cyclic voltammetry analysis electrode potential studies suggests that Ni I species activate halides via oxidative addition and alkyl single electron transfer.

Language: Английский

Citations

1
Recent progress on electrochemical synthesis involving carboxylic acids DOI

Na Chen,

Zenghui Ye, Fengzhi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(25), P. 5501 - 5520

Published: Jan. 1, 2021

Recent progress on sustainable electrochemical synthesis involving carboxylic acids was reviewed.

Language: Английский

Citations

57
Recent Advances in C(sp3)–C(sp3) and C(sp3)–C(sp2) Bond Formation through Cathodic Reactions: Reductive and Convergent Paired Electrolyses DOI Creative Commons
Aurélie Claraz, Géraldine Masson

ACS Organic & Inorganic Au, Journal Year: 2021, Volume and Issue: 2(2), P. 126 - 147

Published: Dec. 22, 2021

The formation of C(sp3)–C(sp3) and C(sp3)–C(sp2) bonds is one the major research goals synthetic chemists. Electrochemistry commonly considered to be an appealing means drive redox reactions in a safe sustainable fashion has been utilized for C–C bond-forming reactions. Compared anodic oxidative methods, which have extensively explored, cathodic processes are much less investigated, whereas it can pave way alternative retrosynthetic disconnections target molecules discovery new transformations. This review provides overview on recent achievements construction via since 2017. It includes electrochemical reductions convergent paired electrolyses.

Language: Английский

Citations

53