Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis DOI
Aidana Gimnkhan, Rajesh Kancherla, Krishnamoorthy Muralirajan

et al.

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

Published: May 19, 2025

Photocatalytic multicomponent reactions are at the forefront of organic synthesis. In recent years, dicarbofunctionalization olefins has received significant attention, with nickel serving as a key transition metal catalyst under photochemical conditions. However, achieving regioselective 1,4-alkylarylation dienes alkyl and aryl bromides remains challenging. this work, we present Ni/photoredox dual catalysis approach for alkylarylation dienes, offering mild reaction that eliminates need stochiometric reductants. Broad substrate scope mechanistic investigations presented support proposed mechanism.

Language: Английский

Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines DOI Creative Commons

Tian Hongjun,

Feng Jiang,

Xiaoming Wang

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(3)

Published: Jan. 17, 2025

Singly occupied molecular orbital (SOMO) activation of in situ generated enamines has achieved great success (asymmetric) α-functionalization carbonyl compounds. However, examples on the use this mode transformations other functional groups are rare, and combination SOMO with transition metal catalysis is still less explored. In area deoxygenative functionalization amides, intermediates such as iminium ions were often to result formation α-functionalized amines. contrast, direct deoxygenation amides β-functionalized amines highly appealing yet remains scarcely investigated. Here, a arylation aryl halides was developed via multicatalysis iridium/photoredox/nickel/iridium, affording β-aryl high efficiency. The key reaction enamine synergy Ni-catalyzed arylation, which conjunction two compatible Ir-catalyzed reduction processes.

Language: Английский

Citations

1
Modular Access to Chiral Benzylamines via Ni/Photoredox-Catalyzed Multicomponent Cross-Electrophile Coupling DOI

Panting Cao,

Wenhui Xiong,

Tao Yang

et al.

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

Published: Jan. 30, 2025

A Ni/photoredox dual-catalyzed multicomponent cross-electrophile coupling of N-vinyl amides with (hetero)aryl halides and (2°, 3°)-alkyl redox-active esters in the presence cheap reductant Hantzsch ester is reported here. This reductive protocol provides direct access to various synthetically challenging chiral α-arylamides good yields excellent enantioselectivities (up 99% ee, majority exceeding 97% ee), which can be further derived into primary secondary amines. Preliminary experimental studies shed light on potential catalytic pathways.

Language: Английский

Citations

1
Synthesis of α-Chloroboronic Esters via Photoredox-Catalyzed Chloro-Alkoxycarbonylation of Vinyl Boronic Esters DOI
Wen‐Duo Li, Nana Wei, Nan Feng

et al.

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

Published: March 9, 2025

α-Chloroboronic esters are a class of stable multifunctional molecules that show unique applications in pharmaceutical science and organic chemistry. Despite their apparent utility, the synthetic methods these compounds remain limited. Herein, novel strategy for efficient synthesis α-chloroboronic is developed via photoredox-catalyzed chloro-alkoxycarbonylation vinyl boronic esters. This features advantages high atom economy, environmental friendliness, excellent functional group compatibility was verified by cross-coupling variety free alcohols, oxalyl chlorides, Control experiments mechanistic studies indicate alkoxycarbonyl radical α-boryl carbocation key intermediates this transformation.

Language: Английский

Citations

0
Nickel-Catalyzed Enantioselective Three-Component 1,2-Alkylarylation of Alkenes with Arylboronic Acids as Arylation Reagents DOI
Zhaodong Zhu, Jingjing Wu

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7833 - 7841

Published: April 25, 2025

Language: Английский

Citations

0
Enantioselective Synthesis of Chiral γ‐Amino Acid Esters via Photoredox/Nickel‐Catalyzed Aryl‐Aminoalkylation of Alkenes DOI
Ye Fu, Youzhi Xu,

Songlin Zheng

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 2, 2025

Comprehensive Summary Chiral γ ‐amino acids are among the most valuable and ubiquitous structural units in natural products, pharmaceuticals many physiologically active compounds. Herein, we demonstrate a convenient synthetic approach to chiral acid structures via an asymmetric aryl‐aminoalkylation of alkenes enabled by dual photoredox/nickel catalysis. Taking advantage mild redox‐neutral condition, high levels enantiocontrol α ‐carbonyl benzylic stereocenters obtained. Experimental computational mechanistic studies were performed gain insights into mechanism origin enantioselectivity. The results reveal that reaction follows Ni(0)/Ni(I)/Ni(III)/Ni(I) catalytic cycle C–X bond oxidative addition is enantiodetermining step.

Language: Английский

Citations

0
Nickel/Photoredox Dual-Catalyzed, Regioselective 1,2-Carboacylation of Alkenes via Synergistic Alkyl and Benzoyl Radical Coupling DOI

Xian‐Chen He,

Jie Gao, Yang Li

et al.

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

Published: May 2, 2025

A regioselective 1,2-carboacylation protocol of alkenes via nickel/photoredox dual catalysis has been successfully developed under mild conditions. wide range alkyl bromides, α-oxocarboxylic acids, and styrenes proved to be compatible the optimized conditions, affording corresponding products in up 91% yields. Mechanistically, key success this approach is temporal orchestration radical generation: nickel-catalyzed halogen atom transfer (XAT) for bromides photoredox-driven decarboxylation acids.

Language: Английский

Citations

0
Selective Alkylarylation Difunctionalization of 1,3-Butadienes via Nickel/Photoredox Dual Catalysis DOI
Aidana Gimnkhan, Rajesh Kancherla, Krishnamoorthy Muralirajan

et al.

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

Published: May 19, 2025

Photocatalytic multicomponent reactions are at the forefront of organic synthesis. In recent years, dicarbofunctionalization olefins has received significant attention, with nickel serving as a key transition metal catalyst under photochemical conditions. However, achieving regioselective 1,4-alkylarylation dienes alkyl and aryl bromides remains challenging. this work, we present Ni/photoredox dual catalysis approach for alkylarylation dienes, offering mild reaction that eliminates need stochiometric reductants. Broad substrate scope mechanistic investigations presented support proposed mechanism.

Language: Английский

Citations

0