Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines DOI

Cheng-Jing Li,

Mengyu Liu, Zhonglin Wei

et al.

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

Published: Dec. 11, 2024

A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key the success of this practical protocol relies not only on a bifunctional role dithionite, that is, serving as radical initiator SO

Language: Английский

Copolymerization Involving Sulfur-Containing Monomers DOI
Tian‐Jun Yue, Wei‐Min Ren, Xiao‐Bing Lu

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(24), P. 14038 - 14083

Published: Nov. 2, 2023

Incorporating sulfur (S) atoms into polymer main chains endows these materials with many attractive features, including a high refractive index, mechanical properties, electrochemical and adhesive ability to heavy metal ions. The copolymerization involving S-containing monomers constitutes facile method for effectively constructing polymers diverse structures, readily tunable sequences, topological structures. In this review, we describe the recent advances in synthesis of via or multicomponent polymerization techniques concerning variety monomers, such as dithiols, carbon disulfide, carbonyl sulfide, cyclic thioanhydrides, episulfides elemental (S8). Particularly, significant focus is paid precise control main-chain sequence, stereochemistry, structure achieving high-value applications.

Language: Английский

Citations

47
Arylthianthrenium Salts as the Aryl Sources: Visible Light/Copper Catalysis-Enabled Intermolecular Azidosulfonylation of Alkenes DOI
Hao Xu, Xufeng Li, Yifei Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1845 - 1850

Published: Feb. 26, 2024

The difunctionalization of alkenes using aryl thianthrenium salts as the sources has been reported sporadically. However, four-component on basis not thus far and still remains a challenge. Herein, visible light/copper catalysis-enabled reaction salts, DABCO·(SO

Language: Английский

Citations

24
Photoinduced Vicinal Sulfamoyloximation of Alkenes: Harnessing Bifunctional Nitrosamines via a Rapid Radical Trapping Strategy DOI
Wei Li,

Chenchen Diao,

Yilian Lu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6253 - 6258

Published: July 17, 2024

We developed a photoinduced method for vicinal sulfamoyloximation of alkenes using

Language: Английский

Citations

7
Photoredox-Catalyzed Radical–Radical Cross-Coupling of Sulfonyl Chlorides with Trifluoroborate Salts DOI

Sheng-Ping Liu,

Yan‐Hong He, Zhi Guan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(15), P. 11161 - 11172

Published: July 25, 2023

Sulfones are widely found in natural products and drug molecules. Here, we disclose a strategy for direct synthesis of sulfone compounds with diverse structures by visible-light-catalyzed radical-radical cross-coupling sulfonyl chlorides trifluoroborate salts. Allyl, benzyl, vinyl, aryl trifluoroborates can be successfully cross-coupled (hetero)aryl alkyl chlorides, respectively. This features redox neutrality, good substrate generality, simple operation, benign reaction conditions.

Language: Английский

Citations

12
Ni-Catalyzed Hydrosulfonylation of Alkenes with Aromatic Iodides and K2S2O5 DOI
Jun Zhang,

Hui-Ling Ma,

Chenxi Yang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(44), P. 8043 - 8047

Published: Oct. 30, 2023

Hydrosulfonylation of alkenes with readily available aromatic iodides via a SO2-insetion strategy is presented. The combination non-noble Ni catalysis (iPr)3SiH as the final reductant enables efficient formation aryl and heteroaryl sulfinate intermediates, which undergo Michael-type additions to electron-deficient for initiating hydrosulfonylation process. Moreover, superiority this protocol demonstrated by broad substrate scope good functional group compatibility.

Language: Английский

Citations

12
An Aqueous Three‐Component Reaction of Cyclopropanols, DABCO ⋅ (SO2)2 and Diaryliodonium salts DOI

Yanjie Qiu,

Jiating Yao,

Hongguang Xia

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(19), P. 3392 - 3396

Published: Sept. 14, 2023

Abstract An additive‐ and external oxidant‐free reaction of cyclopropanols, DABCO ⋅ (SO 2 ) diaryliodonium salts in aqueous phase is described. This proceeds under mild conditions, affording bioactive aryl substituted γ‐keto sulfones 36%‐90% yields with good functional group tolerance. through a sulfinate intermediate, which undergoes nucleophilic salts, giving rise to corresponding sulfones.

Language: Английский

Citations

9
Sequential Ring Opening/In Situ SO2-Capture/Alkynylation of Cyclopropanols with Alkynyl Triflones Initiated by Energy Transfer DOI
Guohua Fan,

Changfu Wu,

Xiaozu Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7656 - 7661

Published: May 15, 2024

A visible-light-triggered ring opening/in situ SO2-capture/alkynylation sequence of cyclopropyl alcohols with alkynyl triflones using 4CzIPN as a triplet energy transfer photocatalyst is herein described. This metal-free protocol provides straightforward and atom-economical approach to alkynyl-substituted γ-keto sulfones broad scope substituents. In this transformation, could be used both radical acceptors SO2 donors. Preliminary experimental mechanistic studies synthetic utility are also demonstrated.

Language: Английский

Citations

3
Access to chiral sulfones with an all-carbon quaternary stereocenter from sulfur dioxide DOI

Chunxi Huang,

Xuemei Zhang, Liping Luo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4275 - 4283

Published: Jan. 1, 2024

A copper-catalyzed enantioselective four-component reaction via the insertion of sulfur dioxide toward synthesis chiral sulfones bearing an all-carbon quaternary stereocenter at β position is reported.

Language: Английский

Citations

3
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
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