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CC BY 4.0 · SynOpen 2024; 08(04): 360-386
DOI: 10.1055/a-2446-9165
DOI: 10.1055/a-2446-9165
graphical review
Recent Advances in Chlorination: Novel Reagents and Methods from the Last Decade
This work received financial support from Fundação para a Ciência e Tecnologia and Ministério da Ciência, Tecnologia e Ensino Superior (FCT/MCTES) through PT national funds projects (PTDC/QUI-QOR/1131/2020, and LAQV-REQUIMTE UIDB/50006/2020, UIDP/50006/2020). I.V. acknowledges Fundação Calouste Gulbenkian for the ‘Novos Talentos’ funding program.
Abstract
Chlorinated compounds are vital in organic synthesis, impacting nucleophilic substitutions, β-elimination, and C–H acidity. Herein, recent advances in (hetero)arene chlorination, focusing on novel reagents and methods developed in the past decade, are showcased. Traditional electrophilic agents such as Cl2 and PCl5 have been expanded with new chlorinating agents such as Palau’chlor, as well as with electrochemical and photochemical techniques. Biocatalyzed chlorination using FAD-dependent halogenases has also been explored. Key trends include green chemistry with eco-friendly chlorine sources like NaCl and HCl. Although nucleophilic chlorination remains rare, electrochemical methods show promise, despite equipment limitations. This graphical review highlights significant progress in the last decade towards more sustainable and efficient chlorination strategies.
Key words
(hetero)arene chlorination - electrophilic substitution - nucleophilic chlorination - chlorinating agents - electrochemistry - photocatalysis - biocatalysis - green chemistryPublication History
Received: 23 September 2024
Accepted after revision: 18 October 2024
Accepted Manuscript online:
21 October 2024
Article published online:
19 December 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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