Bifunctionalization of styrene through ring-opening-recombination strategy of phenylpropathiazole salt DOI

Yongbo Fan,

Shengting Xu,

Xinxin Cai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(37), P. 7593 - 7596

Published: Jan. 1, 2023

The ring-opening of a benzothiazole salt serves as sulfur source for the bifunctional reaction styrene, enabling simultaneous formation new C–S, C–O, and CO bonds following C–S bond cleavage.

Language: Английский

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes DOI
Pei Qu,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7485 - 7507

Published: Jan. 1, 2023

The recent advances on the electrochemical selenofunctionalization of unsaturated C–C bonds were comprehensively summarized in this review.

Language: Английский

Citations

32

Electrochemical selenofunctionalization of unactivated alkenes: access to β-hydroxy-selenides DOI
Anil Balajirao Dapkekar, Gedu Satyanarayana

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1775 - 1781

Published: Jan. 1, 2024

This work demonstrates the electrochemical construction of 2-methyl-1-aryloxy-3-(arylselanyl)propan-2-ol/2-hydroxy-2-methyl-3-(arylselanyl)propyl 2-(2-hydroxy-2-methyl-3-(arylselanyl)propoxy)benzoate starting from aryl allyl ethers/allyl benzoates and diaryl diselenides under additive-free conditions. environmentally friendly method was achieved through constant current electrolysis in an undivided cell setup acid, oxidant, or catalyst-free Additionally, this technique enabled synthesis a variety β-hydroxy selenides including late-stage functionalization drug derivatives good to exceptional yields across various substrates mild reaction

Language: Английский

Citations

8

Selectfluor-Mediated Electrophilic Annulation of 2-Alkynyl Biaryls with Diorganyl Diselenides DOI

Qing-Xia Luo,

Hong‐Tao Ji,

Yuhan Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 16790 - 16796

Published: Nov. 28, 2023

A general and efficient method for the synthesis of various selanyl phenanthrenes/polycyclic heteroaromatics through electrophilic annulation 2-alkynyl biaryls with diorganyl diselenides under metal-free mild conditions was established. The sulfanyl phenanthrene also obtained in moderate yields.

Language: Английский

Citations

22

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions DOI

Liguo Lu,

Dayun Huang, Zefeng Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(14), P. 2310 - 2331

Published: June 24, 2023

Abstract Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur‐containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three‐component reactions. It will reduce the number steps and waste generation, form complicated molecules from simple starting materials. Herein, recent developments (2013–2022) have been summarized two categories: (1) selenylation seleniranium intermediates Se‐centered radicals; (2) thiolation more diverse mechanisms products Reactions electron‐rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, sulfamides, TMSNCS, TMSN Et N ⋅ 3HF, SOCl 2 HCl, NFSI, t BuONO, pyridinium salts, BuOOH, ArN BF 4 CO CO, O CF SO Cl, R P(O)−H, (RO) P(O)SH, P(O)OH et al discussed. We hope this review do help for future research area.

Language: Английский

Citations

15

Oxidative Three-Component Selenofunctionalization of Alkenes: Convenient Access to Vicinally Functionalized Selenides DOI
Yun‐Qian Zhang,

You‐Qin Jiang,

Yong‐Hao Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7431 - 7447

Published: May 23, 2023

Three-component selenofunctionalization processes of olefins, diselenides and sulfonamides, water, alcohols, or acids utilizing 1-fluoropyridinium triflate (FP-OTf) as a reaction promoter are reported. Under the optimal conditions, broad range vicinally functionalized selenide derivatives was accessible with high yields excellent functional group compatibilities. Mechanistic studies revealed that FP-OTf played key role in this process.

Language: Английский

Citations

12

PVP‐I Catalyzed Hydroxysulfurization of α‐(Trifluoromethyl)‐Styrenes with Thiols: Access to Trifluoromethyl Tertiary Alcohol DOI Open Access

Qian‐Ding Zeng,

Xinxin Yuan, Jian Wang

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(6)

Published: Feb. 1, 2025

Abstract An efficient method for the synthesis of β ‐hydroxy‐ ‐CF 3 ‐thioether has been developed, utilizing povidone‐iodine (PVP‐I) as a recyclable catalyst and air oxidant. The reaction proceeded smoothly at room temperature, yielding desired in moderate to good yields. This can be scaled up gram‐scale without losing any efficiency. was also 8 repetitions. mechanism investigated plausible pathway proposed.

Language: Английский

Citations

0

One-Pot, Metal-Free Synthesis of Allyl Sulfones in Water DOI
Yunfei Jia, Ping Jiang, Xinqian Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 835 - 843

Published: Jan. 9, 2024

A one-pot dehydration cross-coupling reaction between allyl alcohols and sodium sulfinates that provides sulfones in good to excellent yields is presented. Its broad substrate scope includes symmetrical asymmetrical α,α-diaryl- α-aryl-substituted allylic aryl alkyl sulfinates. For substrates, the E isomer predominates with examples of stereoselectivity. Control experiments provide basis for a proposed radical-mediated mechanism. The metal-free procedure applies cheap commercially available tetrabutylammonium tribromide as catalyst H2O solvent. Notable features this simple, efficient, weakly toxic, environmentally benign strategy include mild convenient operating conditions readily accessible starting materials.

Language: Английский

Citations

3

Synthesis of β‐Hydroxyselenides via Electrochemical Hydroxyselenenylation of Alkenes with Diselenides and H2O DOI
Weiwei Li, Yingyuan Hu,

Junsheng Hou

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(5)

Published: Feb. 2, 2024

Abstract A practical electrochemical method for the synthesis of β‐hydroxyselenides has been developed under an external oxidant‐free condition at room temperature air from alkenes with diselenides and H 2 O. radical mechanism is proposed this transformation gram‐scale reactions demonstrate practicability reaction.

Language: Английский

Citations

3

Electrochemical Oxidative Dehydrogenative Coupling of Sulfoximines to Construct N‐sulfenyl and N‐phosphinyl Sulfoximines DOI
Xiaoman Li, Jiawei Huang, Liang Xu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4647 - 4653

Published: Nov. 6, 2023

Abstract Herein, an electrochemical oxidative approach for the synthesis of N‐sulfenyl and N‐phosphinyl sulfoximines has been established from readily available NH‐sulfoximines with thiophenols diarylphosphine oxides. Utilizing synergistic effect halide salt oxidation, desired products are obtained at room temperature in absence any acidic/basic/metallic additives.

Language: Английский

Citations

7

Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions DOI
Yongsheng Tian,

Lanfeng Wei,

Jiawei Huang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1987 - 1987

Published: Jan. 1, 2024

Language: Английский

Citations

2