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

Fei Wu, Bo Wang, Na-Qi Li, Hui-Yi Yang, Zhi-Hui Ren and Zheng-Hui Guan ()
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Fei Wu: Northwest University
Bo Wang: Northwest University
Na-Qi Li: Northwest University
Hui-Yi Yang: Northwest University
Zhi-Hui Ren: Northwest University
Zheng-Hui Guan: Northwest University

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract 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.

Date: 2023
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DOI: 10.1038/s41467-023-38748-3

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