Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2313 - 2382

Published: Jan. 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.

Language: Английский

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Counter Electrode Reactions—Important Stumbling Blocks on the Way to a Working Electro‐organic Synthesis

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(47)

Published: June 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.

Language: Английский

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Radical approaches to C–S bonds

Nature Reviews Chemistry, Journal Year: 2023, Volume and Issue: 7(8), P. 573 - 589

Published: June 21, 2023

Language: Английский

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Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(2), P. 338 - 366

Published: Jan. 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

Language: Английский

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Dual Roles of Supporting Electrolytes in Organic Electrosynthesis

ChemElectroChem, Journal Year: 2024, Volume and Issue: 11(8)

Published: Jan. 18, 2024

Abstract Synthetic electro‐organic chemistry is advancing to a well‐established methodology in academic research and industry. The simple process control minimizes reagent waste avoids using toxic environmentally unfriendly redox agents, providing feasible sustainable alternative conventional techniques. However, fundamental disadvantage, the necessity of ion‐conductive components within electrolyte. recovery these supporting electrolytes, as well product isolation, pose challenges for work‐up strategies. This review presents following electrochemical protocols featuring material‐ resource‐saving strategy: dual role electrolytes conductivity enabling reagents or meditators. first conclude categorize strategies electrolytes. It may inspire electrochemists advance development optimization synthesis towards more resource‐efficient reaction control.

Language: Английский

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Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(22), P. 4878 - 4902

Published: Sept. 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.

Language: Английский

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Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO₂

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(37)

Published: July 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.

Language: Английский

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Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation

RSC Advances, Journal Year: 2022, Volume and Issue: 12(10), P. 6214 - 6233

Published: Jan. 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

Language: Английский

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Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide

Chemical Science, Journal Year: 2022, Volume and Issue: 13(30), P. 8834 - 8839

Published: Jan. 1, 2022

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

Language: Английский

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

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(39), P. 21189 - 21196

Published: Sept. 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.

Language: Английский

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