Photocatalytic Sulfonylation: Innovations and Applications

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Language: Английский

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Oxo-Sulfonylation of 1,7-Enynes via a Multicomponent Oxidative Radical Polar Crossover Approach

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

Diastereoselective synthesis of trans-3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein vinyl carbocation intermediate undergoes nucleophilic substitution to afford corresponding keto functional group. Deprotection N-Ts group, gram-scale synthesis, other synthetic applications were illustrated. Control experiments mechanistic studies show that water acts as nucleophile in this reaction.

Language: Английский

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C(sp³)–H/C(sp³)–H Dehydrogenative Radical Coupling of Glycine Derivatives

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7577 - 7582

Published: Oct. 10, 2022

Here we report a general C(sp3)–H/C(sp3)–H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons through combination SET HAT process.

Language: Английский

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Photomediated Radical Cascade Addition–Cyclization of N-Butenoyl Tetrahydroquinolines: Accessing Functionalized Julolidines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein, we describe the photomediated radical cascade addition-cyclization of N-butenoyl tetrahydroquinolines to access various functionalized julolidine-5-one. The scope methodology was illustrated with several sulfonyl chlorides and tetrahydroquinolines. Other precursors, such as trifluoromethyl, bromoacetonitrile, bromoacetates, etc., also worked efficiently, demonstrating broad utility method. Finally, large-scale synthesis sulfonyl-substituted julolidine-5-one downstream conversions synthesized julolidine derivatives were carried out illustrate synthetic methodology.

Language: Английский

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Visible‐Light‐Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(35)

Published: Aug. 12, 2022

Abstract A new photoinduced acylation/arylation of N ‐(arylsulfonyl)acrylamide with acyl oxime esters through a nitrogen‐centered radical protocol has been disclosed for efficient preparation functionalized indolin‐2‐ones, which proceeds cascade addition carbon‐carbon double bond, aryl migration, desulfonylation, and intramolecular cyclization sequence. This redox‐neutral strategy features excellent selectivity, good substituent tolerance, wide substrate scope.

Language: Английский

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