Synthesis 2019; 51(07): 1680-1688
DOI: 10.1055/s-0037-1610675
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Carbonylation of Coumarin C(sp2)–H Bonds: A New Entry to Arylcoumarin Ketones

Siyavash Mirzaei
a   Department of Genetics, Royan Institute for Reproductive Biomedicine, ACECR, Tehran, Iran
,
Saideh Rajai-Daryasarei
b   School of Chemistry, College of Science, University of Tehran, Tehran, Iran
,
Mehdi Soheilizad
c   CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
,
Roya Kabiri
d   NMR Lab, Faculty of Chemistry, Tabriz University, Tabriz, Iran
,
Samira Ansari
c   CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
,
Meisam Shabanian
e   Faculty of chemistry and petrochemical engineering, Standard Research Institute (SRI) Karaj, Karaj, Iran
,
f   SOHA Pharmaceutical company, Karaj, Iran   Email: pashazadeh.rahim@yahoo.com
› Author Affiliations
We acknowledge the financial support from the SOHA pharmaceutical company and University of Tehran.
Further Information

Publication History

Received: 30 October 2018

Accepted after revision: 05 November 2018

Publication Date:
19 December 2018 (online)


Abstract

A facile and efficient palladium-catalyzed carbonylation of coumarins involving two C–C bond formations has been developed. The C–H bond oxidative functionalization proceeds through aroylation with insertion of carbon monoxide to give arylcoumarin ketones. The reaction conditions, employing ambient pressures of CO gas as C1 feedstock, dramatically improve the generality of the carbonylation of aryl halides.

Supporting Information