Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides

Novel strategy for acid chlorides formation that do not use carboxylic acids is particularly attractive in chemical synthesis but remains challenging. Herein, we reported the development of a highly effective Pd-catalyzed hydrochlorocarbonylation of alkenes with CO for the formation of alkyl acid ch...

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Bibliographic Details
Published in:Nature communications 2023-05, Vol.14 (1), p.3167-3167, Article 3167
Main Authors: Wu, Fei, Wang, Bo, Li, Na-Qi, Yang, Hui-Yi, Ren, Zhi-Hui, Guan, Zheng-Hui
Format: Article
Language:English
Subjects:
639/638/403/933
639/638/77/884
639/638/77/888
Acids
Acylation
Alkenes
Carbonyl compounds
Carbonyls
Carboxylic acids
Chemical reactions
Chemical synthesis
Chlorides
Humanities and Social Sciences
multidisciplinary
Palladium
Science
Science (multidisciplinary)
Substrates
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Summary:Novel strategy for acid chlorides formation that do not use carboxylic acids is particularly attractive in chemical synthesis but remains challenging. Herein, we reported the development of a highly effective Pd-catalyzed hydrochlorocarbonylation of alkenes with CO for the formation of alkyl acid chlorides. Chlorosilane and AcOH were found as a mild HCl source for the reaction. The reaction shows broad substrate scope and produces both branched and linear alkyl acid chlorides in good to high yields upon different ligands and solvents. Cooperating with follow-up acylation reactions, the Pd-catalyzed hydrochlorocarbonylation offers a complementary platform for the synthesis of diverse carbonyl compounds from alkenes. Mechanistic investigations suggested that the reaction proceeded though a palladium hydride pathway, and CO prompted reductive elimination of the acyl-Pd-Cl intermediate. Acid chloride formation is generally limited to the chlorination of carboxylic acids. Here, the authors report a palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for the synthesis of various alkyl acid chlorides.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-023-38748-3