Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction

Traditionally employed as hydrogenation reagents, benzothiazolines have emerged as versatile carbanion and radical transfer reagents, playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress in photochemistry and radical chemistry have prompted the study of...

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Main Authors: Xiaotang Chen, Bao-Chen Qian
Format: Article
Language:English
Published: MDPI AG 2025-04-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/30/8/1711
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author Xiaotang Chen
Bao-Chen Qian
author_facet Xiaotang Chen
Bao-Chen Qian
author_sort Xiaotang Chen
collection DOAJ
description Traditionally employed as hydrogenation reagents, benzothiazolines have emerged as versatile carbanion and radical transfer reagents, playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress in photochemistry and radical chemistry have prompted the study of visible light-driven radical reactions, bringing benzothiazolines into a vibrant focus. Their chemical processes have been uncovered to encompass a variety of activation mechanisms, with five distinct modes having been identified. This work reviews the innovative applications of benzothiazolines as donors of alkyl or acyl groups, achieving hydroalkylation or hydroacylation and alkyl or acyl substitution. By examining their diverse activation mechanisms, this review highlights the potential of benzothiazolines serving as alkyl and acyl groups for further research and development. Moreover, this review will offer exemplary applications and inspiration to synthetic chemists, contributing to the ongoing evolution of benzothiazolines utility in organic synthesis.
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spelling doaj-art-b8f294d879a44020ae577fa24be23f902025-08-20T02:28:20ZengMDPI AGMolecules1420-30492025-04-01308171110.3390/molecules30081711Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond ConstructionXiaotang Chen0Bao-Chen Qian1College of Medical Engineering, Jining Medical University, Jining 272000, ChinaCollege of Medical Engineering, Jining Medical University, Jining 272000, ChinaTraditionally employed as hydrogenation reagents, benzothiazolines have emerged as versatile carbanion and radical transfer reagents, playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress in photochemistry and radical chemistry have prompted the study of visible light-driven radical reactions, bringing benzothiazolines into a vibrant focus. Their chemical processes have been uncovered to encompass a variety of activation mechanisms, with five distinct modes having been identified. This work reviews the innovative applications of benzothiazolines as donors of alkyl or acyl groups, achieving hydroalkylation or hydroacylation and alkyl or acyl substitution. By examining their diverse activation mechanisms, this review highlights the potential of benzothiazolines serving as alkyl and acyl groups for further research and development. Moreover, this review will offer exemplary applications and inspiration to synthetic chemists, contributing to the ongoing evolution of benzothiazolines utility in organic synthesis.https://www.mdpi.com/1420-3049/30/8/1711benzothiazolinescarbanion transfer reagentsradical transfer reagentscarbon–carbon bond construction
spellingShingle Xiaotang Chen
Bao-Chen Qian
Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
Molecules
benzothiazolines
carbanion transfer reagents
radical transfer reagents
carbon–carbon bond construction
title Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
title_full Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
title_fullStr Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
title_full_unstemmed Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
title_short Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction
title_sort benzothiazolines acting as carbanion and radical transfer reagents in carbon carbon bond construction
topic benzothiazolines
carbanion transfer reagents
radical transfer reagents
carbon–carbon bond construction
url https://www.mdpi.com/1420-3049/30/8/1711
work_keys_str_mv AT xiaotangchen benzothiazolinesactingascarbanionandradicaltransferreagentsincarboncarbonbondconstruction
AT baochenqian benzothiazolinesactingascarbanionandradicaltransferreagentsincarboncarbonbondconstruction