Iodine Promoted Conversion of Esters to Nitriles and Ketones under Metal-Free Conditions

Jing Xiao; Fengzhe Guo; Yinfeng Li; Fangshao Li; Qiang Li; Zi-Long Tang

doi:10.1021/acs.joc.0c02794

Iodine Promoted Conversion of Esters to Nitriles and Ketones under Metal-Free Conditions

J Org Chem. 2021 Jan 15;86(2):2028-2035. doi: 10.1021/acs.joc.0c02794. Epub 2021 Jan 4.

Authors

Jing Xiao¹, Fengzhe Guo¹, Yinfeng Li¹, Fangshao Li¹, Qiang Li², Zi-Long Tang¹

Affiliations

¹ Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
² Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, No. 1, Hunan Street, Liaocheng, Shandong 252059, China.

PMID: 33397102
DOI: 10.1021/acs.joc.0c02794

Abstract

We report a novel strategy to prepare valuable nitriles and ketones through the conversion of esters under metal-free conditions. By using the I₂/PCl₃ system, various substrates including aliphatic and aromatic esters could react with acetonitrile and arenes to afford the desired products in good to excellent yields. This method is compatible with a number of functional groups and provides a simple and practical approach for the synthesis of nitrile compounds and aryl ketones.