Synthesis 2019; 51(15): 3014-3020
DOI: 10.1055/s-0037-1610702
paper
© Georg Thieme Verlag Stuttgart · New York

A Regioselective Approach to C3-Aroylcoumarins via Cobalt-Catalyzed­ C(sp2)–H Activation Carbonylation of Coumarins

a   SOHA Pharmaceutical Company, PO BOX 31999-98461, Karaj, Iran   Email: pashazadeh.rahim@yahoo.com
,
Saideh Rajai-Daryasarei
b   School of Chemistry, College of Science, University of Tehran, Tehran, Iran
,
Siyavash Mirzaei
c   Department of Genetics, Royan Institute for Reproductive Biomedicine, ACECR, Tehran, Iran
,
Mehdi Soheilizad
d   CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
,
Samira Ansari
d   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
› Author Affiliations
We acknowledge the financial support from the SOHA pharmaceutical company and the University of Tehran.
Further Information

Publication History

Received: 22 January 2019

Accepted after revision: 12 March 2019

Publication Date:
02 April 2019 (online)


Abstract

A new cobalt-catalyzed C–H bond activation of coumarins with aryl halides or pseudohalides and carbon monoxide insertion to give various 3-aroylcoumarin derivatives is described. It is the first time that CO as C1 feedstock is used as the coupling partners in cobalt-catalyzed regioselective coumarin C–H functionalization reactions. Upon activation with manganese powder, the Co catalyzes the C–H bond activation carbonylation reactions of aryl iodides, bromides, and even triflates under mild conditions, providing the regioselective aroylated products in moderate to good yields.

Supporting Information