New Approach to Perthiyl Radicals for the Synthesis of Unsymmetric Disulfides DOI
Zhong Lian,

Fei Zhou,

X. He

et al.

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 9, 2024

Abstract Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report a novel transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks inaugural use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process were verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously.

Language: Английский

Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides DOI

Lu Lin,

Guanhua Pei,

Zhong‐Yan Cao

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: May 25, 2024

Abstract Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, the past decade, a number of aliphatic sulfonyl been identified showing various biological activities. These appealing features brought about significant advancement developing synthetic methods to access fluorides. this review, we will discuss recent developments radical approaches for synthesis

Language: Английский

Citations

12
Generation of perthiyl radicals for the synthesis of unsymmetric disulfides DOI Creative Commons

Fei Zhou,

X. He, Mi Zhou

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

Unsymmetric disulfides are prevalent in natural products and essential medicinal chemistry materials science, but their robust synthesis poses significant challenges. In this paper, we report an expeditous transition-metal-free methodology for synthesizing unsymmetric through the addition of perthiyl radicals to alkenes. This study marks use generating by reacting SO2 with unactivated alkyl (pseudo)halides (Cl/Br/I/OTs). Various primary, secondary tertiary substituted different functional groups successfully function as suitable reactants. The formation involvement reaction process verified mechanistic studies DFT calculations. Overall, method leverages readily available electrophiles alkenes alongside a single setup efficiently form both carbon-sulfur sulfur-sulfur bonds simultaneously. Here, authors novel transition-metalfree

Language: Английский

Citations

0
Transition-Metal-Catalyzed Regiodivergent Sulfonylation of Aziridrines for the Synthesis of β‑Amino Sulfones DOI

Qinqiong Zeng,

Yujia Gong,

X. He

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(22), P. 6340 - 6346

Published: Jan. 1, 2024

We developed the first transition-metal-catalyzed, regiodivergent sulfonylation of aziridines, enabling efficient synthesis diverse β-amino sulfones under mild conditions with broad substrate compatibility and high regioselectivity.

Language: Английский

Citations

3
Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy DOI

Haozhen Zhang,

Wangchuan Xiao,

Fanhong Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 8, 2024

Language: Английский

Citations

3
On the Existence and Relevance of Copper(III) Fluorides in Oxidative Trifluoromethylation DOI
Noel Nebra, Daniel Joven‐Sancho

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: June 24, 2024

Abstract Numerous reports invoke CuIII–F intermediates engaging in oxidative cross-couplings mediated by low/mid-valent copper and formal sources of ‘F+’ oxidants. These elusive typically instable CuIII fluorides have been rarely characterized or spectroscopically identified, making their existence participation within catalytic cycles somehow questionable. We authenticated a stable organocopper(III) fluoride that undergoes Csp–CF3 bond formation upon addition silyl-capped alkynes following 2 e– CuIII/CuI redox shuttle. This finding strongly supports the intermediacy C–C coupling. review herein state art about well-defined enabling cross-coupling reactions. 1 Introduction Brief History Coupling-Competent Fluorides 3 Design an Isolable – yet Reactive Organocopper(III) Fluoride 4 Alkyne Trifluoromethylation: Scope Mechanism 5 Extension to Aryl–CF3 C–Heteroatom Couplings 6 Summary Outlook

Language: Английский

Citations

1
Visible-light-induced copper-catalyzed regiodivergent C(sp3)-sulfonylation of oxime esters with sodium sulfinates DOI
Ben Ma, Zhiyong Chen, Min Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5876 - 5883

Published: Jan. 1, 2024

A visible-light-induced copper-catalyzed regiodivergent sulfonylation of oxime esters with sodium sulfinates under mild conditions is reported, yielding a range useful β-ketosulfones and sulfonated pyrrolines convertible functional groups.

Language: Английский

Citations

1
Photoinduced Aromatization-Driven Deconstructive Fluorosulfonylation of Spiro Dihydroquinazolinones DOI

Wenpeng Yang,

Hong-Jie Miao,

Gang Wang

et al.

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

Published: Nov. 30, 2024

A catalyst-free photoinduced deconstructive fluorosulfonylation cascade of spiro dihydroquinazolinones with DABSO and NFSI is reported. This protocol features mild reaction conditions, good yields excellent functional group tolerance, providing a practical approach to the quinazolin-4(1H)-one-functionalized aliphatic sulfonyl fluorides. In addition, ease gram-scale synthesis versatility SuFEx exchange highlight application potential this protocol.

Language: Английский

Citations

1
Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy DOI

Yu-Yu Tan,

Lin-Heng He,

Wei‐Min He

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109986 - 109986

Published: May 10, 2024

Language: Английский

Citations

0
Copper-catalyzed sulfonamidation of enol silyl ether via SO2 insertion towards the synthesis of β-keto sulfonamides DOI

Qinqiong Zeng,

Yujia Gong,

Xuemei Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3589 - 3595

Published: Jan. 1, 2024

This method offers a simple, effective pathway for synthesizing diverse β-keto sulfonamides with satisfactory yields under mild conditions, showing broad substrate compatibility and good tolerance towards various functional groups.

Language: Английский

Citations

0
Brønsted base catalyzed Reppe sulfonylation reaction DOI
X. He, Xiaohong Wang, Fei Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4740 - 4747

Published: Jan. 1, 2024

The Reppe sulfonylation reaction has remained substantially underexplored. We present a novel method for involving SO 2 insertion, remarkably without the need metal catalysts, instead utilizing Brønsted bases as catalysts.

Language: Английский

Citations

0