Issue 9, 2024

Photocatalytic organosulfur reagent-promoted selective mono-(deutero)hydrodechlorination

Abstract

Selective partial C–Cl bond reduction represents an important strategy for the construction of valuable chlorine-containing skeletons. Herein, we report an efficient and straightforward mono-(deutero)hydrodechlorination strategy of various trichloroacetyl esters and amides for the incorporation of gem-dichloromethyl moieties. The proposed mechanism involves key electron donor–acceptor (EDA) complexes formed between catalytic cyclohexanethiol (CySH) and substrates, which undergo single-electron transfer (SET) processes under blue light irradiation to provide the gem-dichloro radical anion and CyS˙. A gram-scale reaction and late-stage modification of bioactive molecules further demonstrate the potential utility of this methodology.

Graphical abstract: Photocatalytic organosulfur reagent-promoted selective mono-(deutero)hydrodechlorination

Supplementary files

Article information

Article type
Communication
Submitted
09 Mar 2024
Accepted
11 Apr 2024
First published
13 Apr 2024

Green Chem., 2024,26, 5167-5172

Photocatalytic organosulfur reagent-promoted selective mono-(deutero)hydrodechlorination

J. Wang, G. Gao, J. Cheng, J. Li, X. Chen, X. Chen, D. Zhang, H. Li, X. Cai and B. Huang, Green Chem., 2024, 26, 5167 DOI: 10.1039/D4GC01173B

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