Sulfination of Unactivated Allylic Alcohols via Sulfinate–Sulfone Rearrangement DOI Open Access
Yan Wang, Guangming Wu,

Kaiyu Yan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8895 - 8900

Published: Dec. 7, 2023

A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant sulfinate-sulfone rearrangement. Various sulfones could be obtained in good to excellent yields water as the only byproduct. study expands synthetic toolbox for constructing sulfone molecules.

Language: Английский

Copper-Catalyzed Regio- and Enantioselective Protoboration of Allenyl Sulfones to Access Chiral Allylic Sulfones DOI

Peidong Sun,

Xiaomei Kong,

Huang Jing-wen

et al.

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

Published: Feb. 14, 2025

An efficient method for copper-catalyzed asymmetric protoboration of allenyl sulfones with bis(pinacolato)diboron was developed, providing chiral allylic high efficiency and excellent enantioselectivity. Notably, the directing effect sulfone group plays a pivotal role in achieving both regioselectivity

Language: Английский

Citations

1
Enantioselective Synthesis of Allylic Sulfones via Rhodium-Catalyzed Direct Hydrosulfonylation of Allenes and Alkynes DOI
Chieh‐Yu Chang, Aaron Aponick

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 16996 - 17002

Published: June 14, 2024

A highly regio- and enantioselective hydrosulfonylation using commercially available sodium sulfinates is reported, providing the first direct asymmetric rhodium-catalyzed of allenes/alkynes to synthesize chiral allylic sulfones. Ligand screening studies demonstrated indispensable role C1-symmetric P,N-ligand (Rax,S,S)-StackPhim for achieving both high regioselecitivity (>20:1) enantioselectivity (up 97% ee). Notably, operationally simple method mild conditions allow rapid preparation sulfones with a wide scope functional groups. Moreover, use tert-butyldimethylsilyloxymethanesulfinate enables collective synthesis various sulfone derivatives after transformations protected hydroxymethyl product.

Language: Английский

Citations

8
Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides DOI
Wei‐Cheng Yuan, Xiaohui Fu, Yanping Zhang

et al.

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

Published: Feb. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Language: Английский

Citations

0
Pd-Catalyzed Aerobic Synthesis of Allylic Sulfones from Allylic Alcohols and Sulfonyl Hydrazines in Water DOI
Jing Yu, Xiaoyu Yan, Yuying Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10344 - 10348

Published: July 10, 2024

A mild and green synthesis of allylic sulfones from alcohols sulfonyl hydrazines was developed in water media. The simple commercially available Pd(PPh

Language: Английский

Citations

2
Electrochemical oxidative C H sulfonylation of thiophenes: Site-selective access to 2-arylsulfonylthiophenes DOI
Zhijun Yang,

Zhi Qiao,

Xianglin Yu

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 147, P. 155208 - 155208

Published: July 22, 2024

Language: Английский

Citations

1
Electrochemical Oxidative C–H Sulfonylation of Thiophenes: Site-Selective Access to 2-Arylsulfonylthiophenes DOI
Zhijun Yang,

Zhi Qiao,

Xianglin Yu

et al.

Published: Jan. 1, 2024

Language: Английский

Citations

0
Aminosulfonylation of Rhodium Carbene via Ylide Formation and 1,4-Sulfonyl Rearrangement DOI

Jiahui Su,

Meirong Huang,

Zichun Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9592 - 9597

Published: Oct. 29, 2024

We report here the use of pyridin-2-yl benzenesulfonates as sulfonylation reagents in a difunctionalization reaction based on oxy-pyridinium ylide chemistry, providing an effective protocol for installation both sulfonyl group and pyridone moiety into one molecule. Density functional theory (DFT) calculations disclose that process might proceed through sequential metal-bound formation, keto-enol tautomerism, migratory rearrangement group.

Language: Английский

Citations

0
Sulfination of Unactivated Allylic Alcohols via Sulfinate–Sulfone Rearrangement DOI Open Access
Yan Wang, Guangming Wu,

Kaiyu Yan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(49), P. 8895 - 8900

Published: Dec. 7, 2023

A dehydrative cross-coupling of unactivated allylic alcohols with sulfinic acids was achieved under catalyst-free conditions. This reaction proceeded via allyl sulfination and concomitant sulfinate-sulfone rearrangement. Various sulfones could be obtained in good to excellent yields water as the only byproduct. study expands synthetic toolbox for constructing sulfone molecules.

Language: Английский

Citations

1