Phosphine-Free Aminocarbonylation Using Pd/DBU Catalyst: Carbonylative Coupling of Aryl Iodides and Amines

Baptiste Picard; Takahide Fukuyama; Ilhyong Ryu

doi:10.1021/acs.joc.2c02369

Phosphine-Free Aminocarbonylation Using Pd/DBU Catalyst: Carbonylative Coupling of Aryl Iodides and Amines

J Org Chem. 2023 Apr 21;88(8):5220-5225. doi: 10.1021/acs.joc.2c02369. Epub 2022 Dec 16.

Authors

Baptiste Picard¹, Takahide Fukuyama², Ilhyong Ryu^{1

3}

Affiliations

¹ Organization for Research Promotion, Osaka Metropolitan University, Sakai, Osaka 599-8531, Japan.
² Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, Sakai, Osaka 599-8531, Japan.
³ Department of Applied Chemistry, National Yang Ming Chiao Tung University (NYCU), Hsinchu 30010, Taiwan.

PMID: 36525565
DOI: 10.1021/acs.joc.2c02369

Abstract

An improved carbonylation method allowing amide bond formation between aryl iodides and aromatic amines is presented. In contrast to usual methods based on Pd catalysis, this method does not require a phosphine ligand. The catalyst system simply employs bis(dibenzylideneacetone)palladium (0.5 mol %) and DBU (10 mol %). The method was applied to the synthesis of various aromatic amides from aryl iodides and amines, and was scaled to gram order synthesis under as low as 1 atm of carbon monoxide.