Simple and Efficient Synthesis of Allyl Sulfones through Cs2CO3-Mediated Radical Sulfonylation of Morita–Baylis–Hillman Adducts with Thiosulfonates DOI Creative Commons
Raju Jannapu Reddy,

Angothu Shankar,

Md. Waheed

et al.

SynOpen, Journal Year: 2021, Volume and Issue: 05(01), P. 91 - 99

Published: Jan. 1, 2021

Abstract A highly efficient and eco-friendly method has been developed for the synthesis of allyl sulfones using Morita–Baylis–Hillman (MBH) adducts thiosulfonates under mild conditions. The Cs2CO3-promoted radical sulfonylation provided a series in good to high yields with stereoselectivities. wide variety MBH bromides/acetates as well were tolerated reliable scaled-up synthesis. plausible mechanism is proposed rationalize sulfonylation.

Language: Английский

Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation DOI
Ji‐Kang Jin, Kun Wu, Xin-Yi Liu

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(50), P. 21340 - 21349

Published: Dec. 8, 2021

Charge separation plays a crucial role in regulating photochemical properties and therefore warrants consideration designing photocatalysts. Metal-organic frameworks (MOFs) are emerging as promising candidates for heterogeneous photocatalysis due to their structural designability tunability of photon absorption. Herein, we report the design pyrazole-benzothiadiazole-pyrazole organic molecule bearing donor-acceptor-donor conjugated π-system fast charge separation. Further attempts integrate such photosensitizer into MOFs afford more effective photocatalyst (JNU-204). Under visible-light irradiation, three aerobic oxidation reactions involving different oxygenation pathways were achieved on JNU-204. Recycling experiments conducted demonstrate stability reusability JNU-204 robust photocatalyst. Furthermore, illustrate its applications facile synthesis pyrrolo[2,1-a]isoquinoline-containing heterocycles, core skeletons family marine natural products. is an exemplary MOF platform with good absorption, suitable band gap, separation, extraordinary chemical proceeding under irradiation.

Language: Английский

Citations

135

Nickel-Catalyzed Reaction between Vinyl Azides and an Alkyl Sulfonyl Radical Generated from DMSO: Rapid Access to β-Keto Sulfones DOI
Wenhui Yang, Yu Zhou, Ying Tong

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(12), P. 5046 - 5051

Published: March 14, 2024

A sustainable method for the construction of valuable β-keto sulfones lies in reaction between vinyl azides and alkyl sulfonyl radical generated from low-cost comparatively steady bulk chemical dimethyl sulfoxide (DMSO) that has been developed. This strategy features mild economical conditions using inexpensive NiCl2 as catalyst H2O2 green oxidant. The conversion occurs through a sequence ordered processes consisting addition, denitrogen, hydrogen abstraction, hydrolysis. Mechanistic studies indicate sulfinic acid produced DMSO plays an essential role reduction Ni(III). sensitivity assessment gram-scale experiments proceed smoothly to demonstrate robustness practicality this protocol.

Language: Английский

Citations

11

A visible-light photoredox-catalyzed four-component reaction for the construction of sulfone-containing quinoxalin-2(1H)-ones DOI

Yufen Lv,

Jinyun Luo,

Muze Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(19), P. 5403 - 5409

Published: Jan. 1, 2021

A visible-light photoredox-catalyzed four component reaction of quinoxalin-2(1 H )-ones, alkenes, aryldiazonium, and sodium metabisulfite leading to sulfone-containing )-ones has been developed.

Language: Английский

Citations

38

The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies DOI Creative Commons

Bao‐Chen Qian,

Chao-Zhe Zhu,

Guang‐Bin Shen

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(44), P. 39531 - 39561

Published: Oct. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Language: Английский

Citations

27

Atom-economic synthesis of β-ketosulfones based on gold-catalyzed highly regioselective hydration of alkynylsulfones DOI
Elena I. Chikunova, Vadim Yu. Kukushkin, Alexey Yu. Dubovtsev

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(8), P. 3314 - 3320

Published: Jan. 1, 2022

Gold( i )-catalyzed highly regioselective hydration of alkynylsulfones comprises an efficient 100% atom-economic route to β-ketosulfones.

Language: Английский

Citations

24

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

Base-mediated [3 + 2]-cycloannulation strategy for the synthesis of pyrazolo[1,5-a]pyridine derivatives using (E)-β-iodovinyl sulfones DOI
Raju Jannapu Reddy,

Nunavath Sharadha,

Arram Haritha Kumari

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(21), P. 4331 - 4337

Published: Jan. 1, 2022

A unique cycloannulation of ( E )-β-iodovinyl sulfones with 1-aminopyridinium iodide/ N -tosylpyridinium imide followed by detosylation is realized to access 2-substituted-pyrazolo[1,5- a ]pyridines and their 3-sulfonyl analogues in good high yields.

Language: Английский

Citations

19

Switchable In Situ SO2 Capture and CF3 Migration of Enol Triflates with Peroxyl Compounds under Iron Catalysis DOI

Qi-Chao Shan,

Shuai Liu,

Yuncheng Shen

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(36), P. 6653 - 6657

Published: Sept. 1, 2022

Switchable in situ SO2 capture and CF3 migration of enol triflates with peroxyl compounds under iron catalysis are presented. By regulating the structure peroxides, a variety keto-functionalized dialkyl sulfones α-trifluoromethyl ketones were selectively synthesized good yields mild conditions.

Language: Английский

Citations

19

Iron-catalyzed oxosulfonylation of alkynes with small-ring compounds and Na2S2O5 for the synthesis of β-keto sulfones DOI

Liu-Bin Li,

Hui Qiu,

Mu-Han Li

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5190 - 5197

Published: Jan. 1, 2023

An efficient and rapid iron-catalyzed oxosulfonylation of alkynes with small-ring compounds Na 2 S O 5 for the synthesis β -keto sulfones has been developed.

Language: Английский

Citations

12

Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes DOI
Xiang Liu, Yuan Zhang, Yi Zheng

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1367 - 1372

Published: Feb. 23, 2024

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions. electrochemical C—H proceeded smoothly to afford ( E )‐vinyl sulfones good selectivity in an undivided cell without external oxidant. While aerobic trifunctionalization occurred presence KI air, which provides β ‐keto selenosulfones via formation C—O, C—S, and C—Se bonds one‐pot. Following control experiments, a plausible mechanism is proposed rationalize experimental results.

Language: Английский

Citations

4