Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation DOI Open Access

Zhenhui Xu,

Changdi Zheng,

Jie Lin

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)

Published: Aug. 30, 2024

Abstract The control of enantioselectivity in radical cation reactions presents long‐standing challenges, despite a few successful examples. We introduce novel strategy asymmetric counteranion‐directed electrocatalysis to address chemistry. This concept has been successfully demonstrated two reactions: an dehydrogenative indole‐phenol [3+2] coupling and atroposelective C−H/N−H coupling. These have enabled the synthesis benzofuroindolines C−N axially chiral indoles with high yields excellent enantiomeric excesses. Detailed mechanistic studies confirmed radical‐radical mechanism. Moreover, density functional theory (DFT) calculations supported indole as pivotal intermediate, rather than neutral indolyl radical, shedding new light on underlying processes driving these reactions.

Language: Английский

Unlocking the Potential of Oxidative Asymmetric Catalysis with Continuous Flow Electrochemistry DOI
Pengyu Chen, Chong Huang,

Lianghua Jie

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(11), P. 7178 - 7184

Published: March 11, 2024

In the field of catalytic asymmetric synthesis, less-treated path lies in oxidative transformations. The hurdles pinpointing appropriate chemical oxidants and addressing their compatibility issues with catalysts functionalities present significant challenges. Organic electrochemistry, employing traceless electrons for redox reactions, is underscored as a promising solution. However, commonly used electrolysis batch cells introduces its own set challenges, hindering advancement electrochemical catalysis. Here we introduce microfluidic electrochemistry platform single-pass continuous flow reactors that exhibits wide-ranging applicability to various This exemplified through sulfenylation 1,3-dicarbonyls, dehydrogenative C–C coupling, alkene annulation processes. unique properties not only eliminate need but also enhance reaction efficiency reduce use additives electrolytes. These salient features expedite discovery development addition, production facilitated by parallel ensures straightforward upscaling, removing necessity reoptimization across scales, evidenced direct translation from milligram screening hectogram synthesis.

Language: Английский

Citations

15
A Comprehensive Review of Magnetic Nanocatalysts for C−S, C−Se Bond Formation DOI Creative Commons
Radwan Ali, Jianlin Han, Mosstafa Kazemi

et al.

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Abstract This review manuscript examines magnetic nanocatalysts and their pivotal role in forming carbon‐sulfur (C−S) carbon‐selenium (C−Se) bonds. The study delves into the latest advancements synthesis, characterization, application of nanocatalysts, highlighting unique advantages, including enhanced catalytic activity, superior selectivity, easy recovery through separation, which align with principles green chemistry. Through a critical analysis recent research findings, this also explores mechanistic pathways facilitated by these offering insights operational efficiency potential for recyclability. aims not only to catalog current achievements burgeoning field but identify challenges propose future directions developing more efficient, sustainable, versatile systems C−S C−Se bond formation. By encompassing broad spectrum ranging from bare magnets functionalized composite materials, is comprehensive resource researchers engaged organic catalysis, sustainable

Language: Английский

Citations

0
Advances in Asymmetric Electrochemical Synthesis DOI

Chun Gao,

Xin Liu, Minghui Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 673 - 673

Published: Jan. 1, 2024

Language: Английский

Citations

3
Iodine-mediated thio-arylation under electrochemical conditions DOI Creative Commons
Jiajia Yu,

Tong Li,

Qi Sun

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(15), P. 12042 - 12046

Published: Jan. 1, 2025

An efficient iodine-mediated electrochemical construction of C–S bonds under metal-free and chemical oxidant-free conditions.

Language: Английский

Citations

0
Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation DOI Open Access

Zhenhui Xu,

Changdi Zheng,

Jie Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Aug. 30, 2024

The control of enantioselectivity in radical cation reactions presents long-standing challenges, despite a few successful examples. We introduce novel strategy asymmetric counteranion-directed electrocatalysis to address chemistry. This concept has been successfully demonstrated two reactions: an dehydrogenative indole-phenol [3+2] coupling and atroposelective C-H/N-H coupling. These have enabled the synthesis benzofuroindolines C-N axially chiral indoles with high yields excellent enantiomeric excesses. Detailed mechanistic studies confirmed radical-radical mechanism. Moreover, density functional theory (DFT) calculations supported indole as pivotal intermediate, rather than neutral indolyl radical, shedding new light on underlying processes driving these reactions.

Language: Английский

Citations

2
I2 or I2/PIFA one‒pot induced system for rapid synthesis of chalcogenated enamides, uracils or 2-pyridones under mild conditions DOI

Hamdi Sanaa,

Ismaël Dondasse,

Pascal Retailleau

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(28), P. 12793 - 12799

Published: Jan. 1, 2024

An I 2 -mediated β-C(sp )–H chalcogenylation of enamides under mild and rapid conditions has been developed. Sequential addition PIFA led to valuable 5-thio- 5-seleno-2-pyridones with a free C3 position.

Language: Английский

Citations

0
Electrochemical Nickel-Catalyzed Cross-Electrophile Coupling of Alkenyl Triflates with α-Chloroamides DOI
Xi Zhang, Zenghui Ye,

Yicai Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6364 - 6369

Published: July 25, 2024

Cross-electrophile coupling reactions of different electrophiles have been extensively studied but mainly limited to bromides and iodides. Here, we report an electrochemically induced nickel-catalyzed cross-electrophile strategy between alkenyl triflates α-chloroamides in undivided cell under mild reaction conditions, affording the α-functionalized amide derivatives good excellent yields with broad substrate scopes functional group tolerance. The control experiments were conducted, a plausible mechanism was proposed.

Language: Английский

Citations

0
Asymmetric Counteranion‐Directed Electrocatalysis for Enantioselective Control of Radical Cation DOI Open Access

Zhenhui Xu,

Changdi Zheng,

Jie Lin

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 137(1)

Published: Aug. 30, 2024

Abstract The control of enantioselectivity in radical cation reactions presents long‐standing challenges, despite a few successful examples. We introduce novel strategy asymmetric counteranion‐directed electrocatalysis to address chemistry. This concept has been successfully demonstrated two reactions: an dehydrogenative indole‐phenol [3+2] coupling and atroposelective C−H/N−H coupling. These have enabled the synthesis benzofuroindolines C−N axially chiral indoles with high yields excellent enantiomeric excesses. Detailed mechanistic studies confirmed radical‐radical mechanism. Moreover, density functional theory (DFT) calculations supported indole as pivotal intermediate, rather than neutral indolyl radical, shedding new light on underlying processes driving these reactions.

Language: Английский

Citations

0