Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

Dmitrii V Kalinin; Trond Ulven

doi:10.1021/acs.joc.3c00948

Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

J Org Chem. 2023 Dec 1;88(23):16633-16638. doi: 10.1021/acs.joc.3c00948. Epub 2023 Nov 15.

Authors

Dmitrii V Kalinin^{1

2}, Trond Ulven^{1

3}

Affiliations

¹ Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, 5230 Odense, Denmark.
² Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, 48149 Münster, Germany.
³ Department of Drug Design and Pharmacology, University of Copenhagen, 2100 Copenhagen, Denmark.

PMID: 37968936
DOI: 10.1021/acs.joc.3c00948

Abstract

A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C(sp³)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.