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Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones

Dhanarajan Arunprasath, Pandi Muthupandi and Govindasamy Sekar*

*Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamil Nadu, India, Email: gsekariitm.ac.in

D. Arunprasath, P. Muthupandi, G. Sekar, Org. Lett., 2015, 17, 5448-5451.

DOI: 10.1021/acs.orglett.5b02803 (free Supporting Information)


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Abstract

A migratory insertion of carbene followed by a Heck reaction enables the synthesis of 2-arylidene-3-aryl-1-indanones in excellent yields from very stable and easily accessible N-tosylhydrazones and 2′-iodochalcones through 5-exo-trig cyclization that delivers the products selectively with E configuration of the double bond. In situ synthesis of both 2′-iodochalcones and N-tosylhydrazones has also been demonstrated.

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Key Words

indanones


ID: J54-Y2015