Dual Iron and Nickel-Catalyzed Photoelectrochemical C–C Functionalization of Alcohols DOI

Synfacts, Journal Year: 2024, Volume and Issue: 20(10), P. 1067 - 1067

Published: Sept. 13, 2024

Language: Английский

Unified Photocatalytic Strategy for the Cross-Coupling of Alcohols with Aryl Halides Enabled by Synergistic Nickel and Iron LMCT Catalysis DOI

Mohammad Jaber,

Yasemin Ozbay,

Emmanuel Chefdeville

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17), P. 12757 - 12768

Published: Aug. 9, 2024

The use of alcohol feedstock as a coupling partner in cross-coupling reactions offers an extraordinary potential for the efficient synthesis Csp3-rich complex molecular scaffolds. This prominent strategy relies on generation alkoxy radicals, which can react via various radical pathways to give carbon-centered radicals that be engaged C–C bond formation reactions. However, involving catalytic directly from native alcohols are highly challenging and scope existing methods remains particularly limited. Moreover, unified incorporate broad range with aryl halides is currently unavailable. Herein, we report general photocatalytic platform combines nickel iron ligand-to-metal charge transfer (LMCT) catalysis selective deconstructive Csp3–Csp3 cleavage arylation unactivated alcohols. protocol leverages ability photoinduced LMCT generate diversely substituted alcohols, enabling implementation bond-forming manifolds. These include dehydroxymethylative aliphatic remote cyclic yield alkyl ketones, methylation using tertiary methyl source. methodology practical engaging large variety commercially available under mild conditions, abundant catalysts. Mechanistic studies, including stoichiometric organometallic chemistry voltammetry, provide insights into crucial role ancillary ligand surrounding catalyst stabilizing both low- high-valent intermediates.

Language: Английский

Citations

5
Bimetallic Ni/Fe functionalized, 3D printed, self-supporting catalytic-electrodes for CO2 reduction reaction DOI
Jiangyu Sheng,

Mingshu Gao,

Na Zhao

et al.

Fuel, Journal Year: 2024, Volume and Issue: 382, P. 133703 - 133703

Published: Nov. 16, 2024

Language: Английский

Citations

5
Asymmetric Paired Electrolysis: Enantioselective Alkylation of Sulfonylimines via C(sp3)−H Functionalization DOI
Yongsheng Tao,

Wan Ma,

Rui Sun

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(38)

Published: July 3, 2024

Enantioselective transformation of ubiquitous C(sp

Language: Английский

Citations

4
Paired electrolysis enables weak Brønsted base-promoted amination of arenes with N,N-dialkyl formamides as the amine source DOI

Xiaoxia Ye,

Min Liu,

Shi-Yan Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5479 - 5487

Published: Jan. 1, 2024

A paired electrolysis enabled amination of arenes using N , -dialkyl formamides as the amine source for synthesis arylamines without need chemical oxidants, metal catalysts or high temperatures is reported.

Language: Английский

Citations

4
Photoredox/Nickel Dual Catalysis for C(sp2)–C(sp3) Cross-Electrophile Coupling Reaction of Mesylates of Phenols and Primary Alcohols DOI
Sayan K. Jana,

R. N. Bhattacharya,

Purusattam Dey

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14172 - 14182

Published: Sept. 11, 2024

Language: Английский

Citations

4
Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis DOI Creative Commons
Reem Nsouli, Sneha Nayak, Venkadesh Balakrishnan

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(43), P. 29551 - 29559

Published: Oct. 18, 2024

Decarboxylative cross-coupling of carboxylic acids and aryl halides has become a key transformation in organic synthesis to form C(sp

Language: Английский

Citations

4
Mechanistic Insights into the Visible-Light-Driven O–Arylation of Carboxylic Acids Catalyzed by Xanthine-Based Nickel Complexes DOI Creative Commons
Rafael E. Rodríguez‐Lugo,

J. Sander,

Simon Dietzmann

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Experimental and theoretical investigations were conducted to gain insight into the mechanism of light-driven Ni-catalyzed arylation carboxylates.

Language: Английский

Citations

0
Enantioselective Remote Alkylation Enabled by Metallaphotoredox Catalysis via Selective C–C Bond Cleavage DOI
Ao Yu,

Ning Wang,

Siyuan Tang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 2212 - 2221

Published: Jan. 23, 2025

Despite recent advances in enantioselective radical coupling with strained cyclic rings, asymmetric reactions triggered by unstrained motifs remain rare. Herein, we report a mild and general strategy for activating diverse set of readily available alcohols the remote site-specific allylic alkylation ketones through combination photoredox-mediated proton-coupled electron transfer chiral chromium catalysis. This newly developed dual catalytic system exhibits extensive applicability, operates under conditions, offers straightforward operation, demonstrates tolerance to functional groups. The open-shell has also been applied late-stage modification complex drug natural product derivatives high levels enantioselectivity.

Language: Английский

Citations

0
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

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

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2
Redox-neutral decarboxylative coupling of fluoroalkyl carboxylic acids via a dual metal photoelectrocatalysis DOI Creative Commons
Yaxing Wu, Xiuling Wang, Zhenyu Wang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Given the importance and beneficial characteristics of aliphatic CF

Language: Английский

Citations

1