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

Siyavash Mirzaei; Saideh Rajai-Daryasarei; Mehdi Soheilizad; Roya Kabiri; Samira Ansari; Meisam Shabanian; Rahim Pashazadeh

doi:10.1055/s-0037-1610675

Synthesis, Table of Contents

Synthesis 2019; 51(07): 1680-1688
DOI: 10.1055/s-0037-1610675

paper

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

Siyavash Mirzaei

^aDepartment of Genetics, Royan Institute for Reproductive Biomedicine, ACECR, Tehran, Iran

,

Saideh Rajai-Daryasarei

^bSchool of Chemistry, College of Science, University of Tehran, Tehran, Iran

,

Mehdi Soheilizad

^cCinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

,

Roya Kabiri

^dNMR Lab, Faculty of Chemistry, Tabriz University, Tabriz, Iran

,

Samira Ansari

^cCinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran

,

Meisam Shabanian

^eFaculty of chemistry and petrochemical engineering, Standard Research Institute (SRI) Karaj, Karaj, Iran

,

Rahim Pashazadeh *

^fSOHA Pharmaceutical company, Karaj, Iran Email: pashazadeh.rahim@yahoo.com

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Abstract

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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.

Key words

Pd catalysis - carbonylation - arylcoumarin ketones - aryl halides - carbon monoxide.

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References

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