Dual Inert C–H Bond Site-Selective Activations Enabled by Pd/Norbornene-Mediated Cascade Cyclization toward Medium-Sized Polyheterocyclic Methylene Sulfoximines DOI
Wei Li, Xun Fang, Xiaojuan Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(49), P. 10548 - 10552

Published: Nov. 28, 2024

A Pd/norbornene-mediated three-component modular one-step reaction facilitated by dual C-H bond activation and cascade cyclization is reported. This procedure uses norbornene as a catalyst in the Catellani-type an alkylating building block to accomplish unactivated functionalization protocol, which results production of polyheterocyclic eight-membered sulfoximines with indene-fused moiety. mild, scalable protocol's wide substrate range makes it ideal for site-selective at highly chemoselective aryl sites.

Language: Английский

Visible-Light-Induced Sulfonylation Cyclization to Generate Indole-Fused Medium-Sized N-Heterocycles in 2-Me-THF DOI

Tongtong Shi,

Miao Tian, Yanping Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

A novel visible-light-induced sulfonylation cyclization to indole-fused medium-sized N-heterocycles was established under room temperature with biomass-derived 2-Me-THF as the solvent. This reaction proceeds in absence of external photocatalyst, additive, metal salts, and base. Broad substrate scope, good functional group compatibility, large-scale synthesis derivatization via iodination, nitration, chlorination, cyanation, selenylation demonstrate utility this protocol. radical route proposed based on inhibition experiments, visible-light irradiation on-off test, apparent quantum efficiency calculation, UV-vis absorption spectroscopic studies.

Language: Английский

Citations

0

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

Ligand-Modulated Nickel/Photoredox-Catalyzed exo-Arylalkylation of Alkynes DOI

Lijuan Gao,

Jiaqian Zhang, Na Zhang

et al.

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

Published: March 25, 2025

A ligand-modulated synergetic nickel/photoredox-catalyzed exo-arylalkylation of unactivated alkynes was developed that strikingly different from the known endo-arylalkylation activated arylacetylenes. The unique arylalkylation pathway due to formation a π-allyl-Ni complex alkyne where nickel species engaged in distinctive dual-catalytic cycle. exo-alkenylation applied divergent synthesis tryptamines and benzofurylethylamines.

Language: Английский

Citations

0

Recent advances in photoredox/transition metal-catalyzed sulfonylation using sodium sulfinates DOI
Da‐Liang Zhu,

Jie Li,

David James Young

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134733 - 134733

Published: May 1, 2025

Language: Английский

Citations

0

Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes DOI
Xin Zhang, Wei Li,

Yuxiang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5564 - 5572

Published: Jan. 1, 2024

This study reports the electrochemical reaction of vinylcyclopropanes with sulfonyl chlorides, resulting in 1,5-hydrosulfonylation and 1,5-chlorosulfonylation.

Language: Английский

Citations

1

Three-Component Photochemical Cyclization/Dithiocarbamate Formation of gem-Difluoro Quinolin-2(1H)-ones DOI
Fei Chen,

Gangqing Shi,

Yang Zheng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9604 - 9609

Published: Oct. 29, 2024

Herein, a novel visible-light-induced 6-

Language: Английский

Citations

1

Synthesis of Indole- and Benzofuran-Based Benzylic Sulfones by Palladium-Catalyzed Sulfonylation of ortho-Iodoaryl Allenes DOI
Yuan Yin,

Cangzhu Hu,

Jing Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16653 - 16662

Published: Nov. 6, 2024

A highly efficient palladium-catalyzed domino coupling reaction of

Language: Английский

Citations

1

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

Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes DOI
Yingchun Ma,

Ping Yu,

Ruoyu Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

Citations

1

Na2CO3-Promoted Synthesis of Thiocarbamates from Isocyanates and Thiols under Mild Conditions DOI

Yingbin Gong,

Leilei Yan,

Zhiqiang Guo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6277 - 6281

Published: Jan. 1, 2024

A method for the synthesis of thiocarbamates catalyzed by Na 2 CO 3 from isocyanates and thiols was developed, possible mechanism proposed. This has advantages high yield, good tolerance, atom economy mild conditions.

Language: Английский

Citations

0