Direct Photoactivation of Sulfinic Acids to Access Hydrosulfonylation and Arylsulfonylation of Alkenes DOI
Yuxing Zhang,

Xi‐Rui Xia,

Siyu Guo

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

Simple and atom-economical hydrosulfonylation arylsulfonylation of alkenes have been developed using sulfinic acid as both the sulfonyl group source hydrogen atom donor under light irradiation. These reactions feature catalyst-, oxidant-, additive-free conditions, offering a highly practical approach for synthesis diversely functionalized sulfones. Preliminary mechanistic studies indicate that these proceed via photoactivation to generate radical, followed by radical chain process.

Язык: Английский

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis DOI Creative Commons
Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2017 - 2291

Опубликована: Ноя. 23, 2021

We present here a review of the photochemical and electrochemical applications multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms which both an proton exchanged together, often concerted elementary step. As such, MS-PCET can function as non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from wide variety common functional groups. introduction practitioner’s guide reaction design, with emphasis on unique energetic selectivity features that characteristic this class. then chapters oxidative N–H, O–H, S–H, C–H homolysis methods, generation corresponding neutral species. Then, reductive PCET activations involving carbonyl, imine, other X═Y π-systems, heteroarenes, where ketyl, α-amino, heteroarene-derived radicals be generated. Finally, we asymmetric catalysis materials device applications. Within each chapter, subdivide by group undergoing homolysis, thereafter type transformation being promoted. Methods published prior end December 2020 presented.

Язык: Английский

Процитировано

356

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency DOI
Guglielmo Coppola, Serena Pillitteri, Erik V. Van der Eycken

и другие.

Chemical Society Reviews, Год журнала: 2022, Номер 51(6), С. 2313 - 2382

Опубликована: Янв. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Язык: Английский

Процитировано

163

Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst DOI

Wei-Bao He,

Lan-Qing Gao,

Xinjie Chen

и другие.

Chinese Chemical Letters, Год журнала: 2020, Номер 31(7), С. 1895 - 1898

Опубликована: Фев. 8, 2020

Язык: Английский

Процитировано

106

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides DOI

Dao‐Qing Dong,

Qing‐Qing Han,

Shaohui Yang

и другие.

ChemistrySelect, Год журнала: 2020, Номер 5(42), С. 13103 - 13134

Опубликована: Ноя. 13, 2020

Abstract Sodium sulfinates, sulfinic acids, sulfonyl chlorides and hydrazides as readily available efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these via different methods, then the could react with various substrates pathways to afford corresponding products. In this review, we will summarize progress reaction using sodium three terms of reagents, classify reactions into four types: 1. Sulfonylation sulfinates. 2. acid. 3. chlorides. 4. hydrazides.

Язык: Английский

Процитировано

95

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts DOI
Olga M. Mulina, Alexey I. Ilovaisky,

Vadim D. Parshin

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(21), С. 4579 - 4654

Опубликована: Авг. 3, 2020

Abstract Oxidative coupling methodology is widely applied for the formation of carbon‐carbon and carbon‐heteroatom bonds. This review focuses on methods oxidative sulfonylation multiple bonds involving sulfonyl hydrazides, sulfinic acids their salts as reagents. Under conditions, they generate radicals, trapped by resulting in a variety SO 2 ‐containing products: mainly, vinyl alkynyl sulfones, hydroxy‐, keto, halo‐substituted sulfonylated derivatives carbo‐ heterocycles. exhaustive summarizes 321 references from 1996 to 2020 with specialization studies last five years, divided into chapters according classes compounds being sulfonylated. magnified image

Язык: Английский

Процитировано

93

Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones DOI
Shuai Liang,

Kamil Hofman,

Marius Friedrich

и другие.

ChemSusChem, Год журнала: 2021, Номер 14(22), С. 4878 - 4902

Опубликована: Сен. 3, 2021

Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is great interest. Herein, the goal was provide summary on recent developments field sulfone synthesis. Advances existing limitations traditional approaches towards sulfones were reviewed selected examples. Furthermore, novel emerging technologies for more synthesis future directions discussed.

Язык: Английский

Процитировано

92

Visible light-mediated applications of methylene blue in organic synthesis DOI

Roshan I. Patel,

Anoop Sharma, Shivani Sharma

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(7), С. 1694 - 1718

Опубликована: Янв. 1, 2021

This review presents the manipulation of methylene blue in visible-light-assisted organic synthesis.

Язык: Английский

Процитировано

88

Recyclable Perovskite as Heterogeneous Photocatalyst for Aminomethylation of Imidazo‐Fused Heterocycles DOI
Tao Shi, Kai Sun, Xiaolan Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(11), С. 2143 - 2149

Опубликована: Янв. 8, 2020

Abstract A sustainable and cost‐effective protocol for direct aminomethylation of imidazo‐fused heterocycles by decarboxylative coupling reaction N ‐phenylglycines with in the presence CsPbBr 3 under irradiation visible light has been developed. This is first example ‐catalyzed heterocycles. The eminent advantage this work that, easily prepared can be used at least 5 times without obvious reduction its activity, exhibiting high catalyst economic feature. magnified image

Язык: Английский

Процитировано

76

Recent advances in the synthesis and applications of β-keto sulfones: new prospects for the synthesis of β-keto thiosulfones DOI
Raju Jannapu Reddy,

Arram Haritha Kumari,

Jangam Jagadesh Kumar

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(14), С. 3087 - 3118

Опубликована: Янв. 1, 2021

This review highlights recent developments relating to the preparation of β-keto sulfones and thiosulfones. And, also focused on widespread synthetic applications for assembling many valuable carbo- heterocycles.

Язык: Английский

Процитировано

60

Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes DOI

Subham Gupta,

Abhishek Kundu, Sumit Ghosh

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8459 - 8493

Опубликована: Янв. 1, 2023

This review comprehensively summarizes visible light-induced difunctionalization strategies for alkene and alkyne systems in metal-free conditions with literature coverage up to July 2023.

Язык: Английский

Процитировано

40