Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis DOI

Tonglv Pu,

Si‐Hai Wu,

Liuyan Cai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well acetylene has been established by employing N-sulfonyl heteroaromatics bifunctional reagents (BFRs) to efficiently deliver (E)-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition alkynes, sulfonylation processes.

Language: Английский

Sc(OTf)3-Catalyzed Diastereoselective Hydroxyheteroarylation of C–C σ-Bonds of Bicyclo[1.1.0]butanes with Azaheterocyclic N-Oxides DOI
Jiang Wang, Jiajia Liu, Chenwei Li

et al.

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

Published: March 22, 2025

A mild and atom-economical reaction for the Sc(OTf)3-catalyzed 1,3-hydroxyheteroarylation of bicyclo[1.1.0]butanes (BCBs) with azaaryl N-oxides via an unprecedented [4π+2σ] cycloaddition/ring-opening process is described. This transformation provides a novel strategy highly regio- diastereoselective preparation azaheterocycle-tethered 1,1,3,3-tetrasubstituted cyclobutane derivatives offers broad substrate scope high yields.

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
Nickel-Catalyzed Hydrocarbamoylation of Alkenes with Isocyanates DOI

Meng-Ying Qian,

Yuqing Wang, Qi‐Lin Zhou

et al.

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

Published: March 17, 2025

The hydrocarbamoylation of alkenes with isocyanates is a promising method for synthesizing amides. However, applying this strategy to more inert, simple alkenes, such as styrenes, α-olefins, and internal poses significant challenges. Here, we report the first nickel-catalyzed isocyanates, facilitated by triethoxysilane reduce nickelacycle intermediates. By switching ligands─including 6,6′-dimethyl-2,2′-bipyridine N-heterocyclic carbene─this efficiently produces amides from diverse array including gaseous olefins.

Language: Английский

Citations

0
Regio- and Stereoselective β-Sulfonylamination of Alkynes via Photosensitized Bifunctional N–S Bond Homolysis DOI

Tonglv Pu,

Si‐Hai Wu,

Liuyan Cai

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well acetylene has been established by employing N-sulfonyl heteroaromatics bifunctional reagents (BFRs) to efficiently deliver (E)-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition alkynes, sulfonylation processes.

Language: Английский

Citations

1