Abstract
AbstractNovel 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.
Funder
National Natural Science Foundation of China
Publisher
Springer Science and Business Media LLC
Subject
General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary
Reference53 articles.
1. Smith, M. B. & March, J. March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 5th edn (Wiley-Interscience, 2001).
2. El-Faham, A. & Albericio, F. Peptide coupling reagents, more than a letter soup. Chem. Rev. 111, 6557–6602 (2011).
3. Ansell, M. F. In The Chemistry of Acyl Halides (ed. Patai, S.) 35–68 (Interscience, 1972).
4. Cernak, T. A. & Lambert, T. H. Multicatalytic synthesis of α-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reaction. J. Am. Chem. Soc. 131, 3124–3125 (2009).
5. Tung, P. & Mankad, N. P. Light-mediated synthesis of aliphatic anhydrides by Cu-catalyzed carbonylation of alkyl halides. J. Am. Chem. Soc. 145, 9423–9427 (2023).
Cited by
11 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献