Building a Pyrazole–Benzothiadiazole–Pyrazole Photosensitizer into Metal–Organic Frameworks for Photocatalytic Aerobic Oxidation

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(50), С. 21340 - 21349

Опубликована: Дек. 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.

Язык: Английский

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Nickel-Catalyzed Reaction between Vinyl Azides and an Alkyl Sulfonyl Radical Generated from DMSO: Rapid Access to β-Keto Sulfones

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(12), С. 5046 - 5051

Опубликована: Март 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.

Язык: Английский

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

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(19), С. 5403 - 5409

Опубликована: Янв. 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.

Язык: Английский

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

ACS Omega, Год журнала: 2022, Номер 7(44), С. 39531 - 39561

Опубликована: Окт. 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.

Язык: Английский

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Atom-economic synthesis of β-ketosulfones based on gold-catalyzed highly regioselective hydration of alkynylsulfones

Green Chemistry, Год журнала: 2022, Номер 24(8), С. 3314 - 3320

Опубликована: Янв. 1, 2022

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

Язык: Английский

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

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(14), С. 2310 - 2331

Опубликована: Июнь 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.

Язык: Английский

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

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(21), С. 4331 - 4337

Опубликована: Янв. 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.

Язык: Английский

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

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(20), С. 5190 - 5197

Опубликована: Янв. 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.

Язык: Английский

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Recent trends in the synthesis and applications of β-iodovinyl sulfones: a decade of progress

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(13), С. 2492 - 2509

Опубликована: Янв. 1, 2024

Over the past decade, there has been exponential growth in vicinal iodosulfonylation of alkynes using sulfonyl and iodide reactants. This review highlights recent developments β-iodovinyl sulfones their applications organic synthesis.

Язык: Английский

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Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(12), С. 1367 - 1372

Опубликована: Фев. 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.

Язык: Английский

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