Copper-catalyzed direct decarboxylative fluorosulfonylation of aliphatic carboxylic acids DOI

Ji-Tao Yi,

Xiang Zhou, Qilong Chen

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(67), С. 9409 - 9412

Опубликована: Янв. 1, 2022

Sulfonyl fluorides are emerging as key structural motifs in organic synthesis, medicinal chemistry, and materials science. Herein we report two efficient complementary methods for direct decarboxylative fluorosulfonylation of carboxylic acids by the merging copper catalysis with different N-centered HAT regents. A wide range structurally diverse sulfonyl was readily accessed from primary, secondary, tertiary a single step under mild conditions.

Язык: Английский

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

167

Counter Electrode Reactions—Important Stumbling Blocks on the Way to a Working Electro‐organic Synthesis DOI Creative Commons
Martin Klein, Siegfried R. Waldvogel

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(47)

Опубликована: Июнь 7, 2022

Over the past two decades, electro-organic synthesis has gained significant interest, both in technical and academic research as well terms of applications. The omission stoichiometric oxidizers or reducing agents enables a more sustainable route for redox reactions organic chemistry. Even if it is well-known that every electrochemical oxidation only viable with an associated reduction reaction vice versa, relevance counter often less addressed. In this Review, importance corresponding highlighted how can affect performance selectivity electrolytic conversion. A selection common strategies unique concepts to tackle issue are surveyed provide guide select appropriate synthesis.

Язык: Английский

Процитировано

76

Radical approaches to C–S bonds DOI
Zijun Wu, Derek A. Pratt

Nature Reviews Chemistry, Год журнала: 2023, Номер 7(8), С. 573 - 589

Опубликована: Июнь 21, 2023

Язык: Английский

Процитировано

54

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023) DOI
Dan Lehnherr, Longrui Chen

Organic Process Research & Development, Год журнала: 2024, Номер 28(2), С. 338 - 366

Опубликована: Янв. 18, 2024

This review summarizes examples of organic electrosynthesis from the peer-reviewed literature 2000 to 2023 that have been conducted on scales 20 g or above. A significant portion these were a ≤100 scale, while detailed reports kilogram-scale remain scarce in pharmaceutical industry. In addition chemical transformation, this also highlights type reactor used and projected productivity metric as ways compare different reports. The selected scale-ups described herein illustrate remaining challenges currently preventing routine use large-scale

Язык: Английский

Процитировано

44

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

93

Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO2 DOI
Terry Shing‐Bong Lou, Yu Kawamata, Tamara El‐Hayek Ewing

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(37)

Опубликована: Июль 12, 2022

Abstract Simple access to aryl sulfinates from iodides and bromides is reported using an inexpensive Ni‐electrocatalytic protocol. The reaction exhibits a broad scope, uses stock solution of simple SO 2 as sulfur source, can be scaled up in batch recycle flow settings. limitations this are clearly shown put into context by benchmarking with state‐of‐the‐art Pd‐based methods.

Язык: Английский

Процитировано

53

Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation DOI Creative Commons
Pran Gopal Karmaker, Md. Asraful Alam,

Feng Huo

и другие.

RSC Advances, Год журнала: 2022, Номер 12(10), С. 6214 - 6233

Опубликована: Янв. 1, 2022

Techniques utilizing photo- and electrochemically induced reactions have been developed to accelerate organic processes. These techniques use light or electrical energy (electron transfer) as a direct source without using an initiator reagent. Thiocyanates are found in biologically active pharmacological compounds can be converted into various functional groups. It is one of the most prominent scaffolds. Significant development electro-chemically thiocyanation procedures has made recent years for conception carbon-sulfur bonds synthesis pharmaceutically important molecules. This review discusses different driven C(sp

Язык: Английский

Процитировано

51

Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide DOI Creative Commons
Fu‐Sheng He, Chun Zhang, Minghui Jiang

и другие.

Chemical Science, Год журнала: 2022, Номер 13(30), С. 8834 - 8839

Опубликована: Янв. 1, 2022

An organocatalytic enantioselective radical reaction of potassium alkyltrifluoroborates, DABCO·(SO

Язык: Английский

Процитировано

48

One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation DOI

P. Scott Pedersen,

David C. Blakemore,

Gary M. Chinigo

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(39), С. 21189 - 21196

Опубликована: Сен. 20, 2023

The coupling of carboxylic acids and amines to form amide linkages is the most commonly performed reaction in pharmaceutical industry. Herein, we report a new strategy that merges these traditional partners generate sulfonamides, important bioisosteres. This method leverages copper ligand-to-metal charge transfer (LMCT) convert aromatic sulfonyl chlorides, followed by one-pot amination corresponding sulfonamide. process requires no prefunctionalization native acid or amine extends diverse set aryl, heteroaryl, s-rich aliphatic substrates. Further, extend this synthesis (hetero)aryl fluorides, which have found utility as "click" handles chemical probes programmable bifunctional reagents. Finally, demonstrate protocols analogue synthesis.

Язык: Английский

Процитировано

43

Asymmetric sulfonylation with sulfur dioxide surrogates: a new access to enantiomerically enriched sulfones DOI
Jun Zhang, Peiqi Wang, Yanzhi Li

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(26), С. 3821 - 3826

Опубликована: Янв. 1, 2023

In this highlight, we survey recent exciting advances in asymmetric sulfonylation by using sulfur dioxide surrogates, and discuss induction modes, reaction mechanisms, substrate scope opportunities for further studies.

Язык: Английский

Процитировано

33