Consecutive mechanical-force-induced electron transfer for reduction of aryl halides with high reduction potentials DOI Creative Commons
Xiaohong Wang, X. He, Xuemei Zhang

et al.

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

Published: June 4, 2025

Mechanical-force-induced redox catalysis has emerged as a green and expeditous approach in synthetic chemistry, relying on single-electron transfer from polarized piezoelectric materials to substrates initiated by mechanical agitation. However, the potential generated can sometimes be insufficient activate electron process, similar limitations observed photocatalytic reactions. In this work, we introduce catalytic strategy employing consecutive mechanical-force-induced (ConMET) strategy. This uses mechanochemical catalysts with 9-phenyl-dihydroacridine sacrificial donor, enabling efficient transfer. Our method effectively reduces aryl iodides, bromides, even electron-rich chlorides, which possess reduction potentials high -2.8 V (vs. SCE), leading formation of radicals. Ultimately, facilitates anti-Markovnikov hydroarylation alkenes dehalogenative deuteration aromatic halides under mild conditions.

Language: Английский

Catalysis under electric-/magnetic-/electromagnetic-field coupling DOI

Canyu Hu,

Yueyue Dong,

Qianqi Shi

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

This review outlines recent advances in field-regulated catalysis and reveals the key role of dipole manipulation by electric/magnetic/electromagnetic fields.

Language: Английский

Citations

7
Cross-Electrophile Coupling of Aryl Chlorides with Alkyl Chlorides Using Rotating Magnetic Field and Metal Rods DOI
Xiaomei Feng, Xiangye Li, Ning Zhang

et al.

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

Published: April 1, 2025

The pursuit of sustainable and environmentally benign methods techniques continues to challenge organic chemists. Herein, we report the development a novel approach in which electromagnetic induction could participate coupling chlorides using rotating magnetic field metal rods. In particular, describe application this strategy nickel-catalyzed cross-electrophile aryl with alkyl chlorides. Using these abundant commercially available organochlorides, such system allows reactions proceed broader scope than current protocols under mild conditions.

Language: Английский

Citations

1
Catalyst‐Free, Radical Tri‐ and Difluoromethylation of Isocyanides and N‐Arylacrylamides Using Rotating Magnetic Field and Metal Rods DOI Open Access

Xuliang Han,

Haodong Liu,

Xiaomei Feng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Comprehensive Summary The pursuit of sustainable and environmentally benign synthetic methods continues to challenge organic chemists. Herein, we introduce a magnetoredox system for tri‐ difluoromethylation isocyanides N ‐arylacrylamides using rotating magnetic field steel rods. This approach enables facile synthesis functionalized phenanthridines oxindoles without the need catalysts additives under mild conditions. Such potentially represents an attractive strategy selective formation bonds through multifaceted regulation intensity, frequency, rod size.

Language: Английский

Citations

4
Overcoming High Reduction Potentials via Consecutive Mechanical-Force-Induced Electron Transfer Strategy DOI Creative Commons
Zhong Lian, Xiaohong Wang, X. He

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

Abstract Mechanical-force-induced redox catalysis has recently advanced rapidly, emerging as a green and innovative tool in synthetic chemistry. The foundation of this strategy lies the single electron transfer (SET) from polarized piezoelectric materials to substrates, which is initiated by potential generated through mechanical agitation. magnitude primarily influenced intrinsic properties material. In certain circumstances, however, may be insufficient trigger SET process, akin limitations visible-light excitation photocatalytic reactions. This challenge motivated us explore effective solutions. work, we establish catalytic system that utilizes consecutive mechanical-force-induced (ConMET) strategy. novel employs mechanochemical catalysts, with 9-phenyl-dihydroacridine (D1) serving sacrificial donors, facilitating produce significantly more powerful reductive species during grinding. Our approach effectively promotes reduction aryl iodides, bromides even electron-rich chlorides, possess potentials high − 2.8 V (vs. SCE), leading formation radicals. Ultimately, enables anti-Markovnikov hydroarylation alkenes dehalogenative deuteration aromatic halides (Cl, Br) under mild conditions.

Language: Английский

Citations

0
Accommodating Styrenes and Unactivated Olefins: Hydrotrifluoromethylation Using O,O′-Dimethyldithiophosphoric Acid as SET Reductant and H Atom Donor DOI
Chi Gao, Fanyu Kong, Cong Xu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: June 4, 2025

Styrenes are challenging substrates for current trifluoromethyl radical-involved hydrotrifluoromethylation reactions due to competitive side reactions. Moreover, metal-free of olefins that can simultaneously be compatible with styrenes and unactivated aliphatic alkenes is scarce at present. Herein, we describe an air insensitive, mild, broadly applicable protocol by using appropriate redox system comprising chloro(phenyl)trifluoromethyl-λ3-iodane presynthesized O,O'-dimethyldithiophosphoric acid (from P2S5 methanol) addressing these issues.

Language: Английский

Citations

0
Consecutive mechanical-force-induced electron transfer for reduction of aryl halides with high reduction potentials DOI Creative Commons
Xiaohong Wang, X. He, Xuemei Zhang

et al.

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

Published: June 4, 2025

Mechanical-force-induced redox catalysis has emerged as a green and expeditous approach in synthetic chemistry, relying on single-electron transfer from polarized piezoelectric materials to substrates initiated by mechanical agitation. However, the potential generated can sometimes be insufficient activate electron process, similar limitations observed photocatalytic reactions. In this work, we introduce catalytic strategy employing consecutive mechanical-force-induced (ConMET) strategy. This uses mechanochemical catalysts with 9-phenyl-dihydroacridine sacrificial donor, enabling efficient transfer. Our method effectively reduces aryl iodides, bromides, even electron-rich chlorides, which possess reduction potentials high -2.8 V (vs. SCE), leading formation of radicals. Ultimately, facilitates anti-Markovnikov hydroarylation alkenes dehalogenative deuteration aromatic halides under mild conditions.

Language: Английский

Citations

0