Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light

Chlorination is a widely used strategy at the industrial level. Chlorinated products represent indispensable building blocks in synthetic chemistry. Here, we report the synthesis of benzyl chlorides and α-chloro alkyl arenes, mediated by visible light, starting from variously substituted toluenes an...

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Main Authors: Lidia De Luca, Luca Ledda, Andrea Porcheddu, Massimo Carraro, Luisa Pisano, Silvia Gaspa
Format: Article
Language:English
Published: MDPI AG 2025-01-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/30/2/312
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author Lidia De Luca
Luca Ledda
Andrea Porcheddu
Massimo Carraro
Luisa Pisano
Silvia Gaspa
author_facet Lidia De Luca
Luca Ledda
Andrea Porcheddu
Massimo Carraro
Luisa Pisano
Silvia Gaspa
author_sort Lidia De Luca
collection DOAJ
description Chlorination is a widely used strategy at the industrial level. Chlorinated products represent indispensable building blocks in synthetic chemistry. Here, we report the synthesis of benzyl chlorides and α-chloro alkyl arenes, mediated by visible light, starting from variously substituted toluenes and <i>N,N</i>-dichloroacetamide as a chlorinating reagent. This methodology is a valid alternative to the syntheses previously reported in the literature. It is a metal-free process and does not involve the use of additives or radical initiators.
format Article
id doaj-art-36c8f6581fae495a8042b80535aae072
institution Kabale University
issn 1420-3049
language English
publishDate 2025-01-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj-art-36c8f6581fae495a8042b80535aae0722025-01-24T13:43:33ZengMDPI AGMolecules1420-30492025-01-0130231210.3390/molecules30020312Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible LightLidia De Luca0Luca Ledda1Andrea Porcheddu2Massimo Carraro3Luisa Pisano4Silvia Gaspa5Dipartimento di Scienze Chimiche, Fisiche, Matematiche e Naturali, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, ItalyDipartimento di Scienze Chimiche, Fisiche, Matematiche e Naturali, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, ItalyDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Cittadella Universitaria, 09042 Monserrato, ItalyDipartimento di Scienze Chimiche, Fisiche, Matematiche e Naturali, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, ItalyDipartimento di Scienze Chimiche, Fisiche, Matematiche e Naturali, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, ItalyDipartimento di Scienze Chimiche, Fisiche, Matematiche e Naturali, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, ItalyChlorination is a widely used strategy at the industrial level. Chlorinated products represent indispensable building blocks in synthetic chemistry. Here, we report the synthesis of benzyl chlorides and α-chloro alkyl arenes, mediated by visible light, starting from variously substituted toluenes and <i>N,N</i>-dichloroacetamide as a chlorinating reagent. This methodology is a valid alternative to the syntheses previously reported in the literature. It is a metal-free process and does not involve the use of additives or radical initiators.https://www.mdpi.com/1420-3049/30/2/312benzyl chloridevisible lighttoluene
spellingShingle Lidia De Luca
Luca Ledda
Andrea Porcheddu
Massimo Carraro
Luisa Pisano
Silvia Gaspa
Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
Molecules
benzyl chloride
visible light
toluene
title Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
title_full Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
title_fullStr Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
title_full_unstemmed Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
title_short Metal-Free Synthesis of α-H Chlorine Alkylaromatic Hydrocarbons Driven by Visible Light
title_sort metal free synthesis of α h chlorine alkylaromatic hydrocarbons driven by visible light
topic benzyl chloride
visible light
toluene
url https://www.mdpi.com/1420-3049/30/2/312
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