Divergent Reaction of Alkynes and TsCN: Synthesis of β-Sulfinyl Alkenylsulfones and (E)-Vinyl Sulfones DOI

Guiting Peng,

Xin Yu, Jiang Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12159 - 12169

Published: Aug. 16, 2024

An efficient and high-selectivity approach for the divergent synthesis of β-sulfinyl alkenylsulfones (E)-vinyl sulfones from alkynes TsCN is described. A series disulfurized products were constructed under mild conditions in absence transition metals. This transformation featured excellent regio- stereoselectivity, good functional group compatibility, broad substrate scope. The copper(I)-catalyzed sulfonation with that affords to yields was also developed.

Language: Английский

Photocatalytic Sulfonylation: Innovations and Applications DOI
Anxiang Huang,

Rui Li,

Qi‐Yan Lv

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

Citations

13
Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C–H Functionalization DOI Creative Commons
Alex S. Anderton, Oliver J. Knowles, James A. Rossi‐Ashton

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(4), P. 2395 - 2401

Published: Jan. 31, 2024

Functionalized sulfides are important in many areas of science, ranging from chemical biology through drug discovery to organic materials chemistry. Sulfides bearing pendant reactive groups the α-position particularly useful; however, methods for selective valorization simple or late-stage functionalization complex by convenient addition valuable functionality underexplored. Here we exemplify a general reaction platform sulfide showcasing three modes α-sulfur C-H functionalization; cyanation, alkenylation, and alkynylation. Using inexpensive commercially available riboflavin tetraacetate visible light, decoration both feedstock proceeds good yield with high selectivity. Methionine-containing peptides can also be selectively functionalized tolerance screen using amino-acid dopants suggests that is compatible most side chains thus potential tool bioconjugation.

Language: Английский

Citations

10
Photocatalytic C–C Bond Azidation and Cyanation of Acyclic Ketones via a Pro-aromatic Intermediate DOI
Sandip Bag,

Amit Dhibar,

Shruti Moorthy

et al.

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

Published: Jan. 10, 2025

Herein, we report a formal C–C bond azidation and cyanation of unactivated aliphatic ketones using commercially available tosyl azide cyanide, respectively. A visible-light-mediated organophotocatalyst enables radical ketone-derived pro-aromatic dihydroquinazolinones (under mostly redox-neutral conditions) as supported by preliminary mechanistic studies. These metal-free scalable protocols can be used to synthesize tertiary, secondary, primary alkyl azides nitriles with good functional group tolerance postsynthetic diversification the group, including bioconjugation.

Language: Английский

Citations

1
Nickel-catalysed Regio- and Stereoselective Hydrocyanation of Alkynoates and Its Mechanistic Insights Proposed by DFT Calculations DOI
Shigeru Arai, Koichi Nakazawa, Xiaofei Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3606 - 3610

Published: Jan. 1, 2024

This work discloses the origin of regio- and stereoselectivity hydrocyanation alkynoates.

Language: Английский

Citations

3
The application and development of cyanating reagents in asymmetric cyanation reactions DOI
Ruirui Hua, Chukai Shao, Fu‐Xue Chen

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155549 - 155549

Published: March 1, 2025

Language: Английский

Citations

0
Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water DOI

Guiting Peng,

Fang Wei, Jiang Bai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Language: Английский

Citations

0
Divergent Reaction of Alkynes and TsCN: Synthesis of β-Sulfinyl Alkenylsulfones and (E)-Vinyl Sulfones DOI

Guiting Peng,

Xin Yu, Jiang Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12159 - 12169

Published: Aug. 16, 2024

An efficient and high-selectivity approach for the divergent synthesis of β-sulfinyl alkenylsulfones (E)-vinyl sulfones from alkynes TsCN is described. A series disulfurized products were constructed under mild conditions in absence transition metals. This transformation featured excellent regio- stereoselectivity, good functional group compatibility, broad substrate scope. The copper(I)-catalyzed sulfonation with that affords to yields was also developed.

Language: Английский

Citations

2