Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones.
A domino process that converges the migratory insertion of carbene with a Heck reaction has been established as a versatile tool for the synthesis of 2-arylidene-3-aryl-1-indanones from very stable and easily accessible N-tosylhydrazones and 2'-iodochalcones. The reaction selectively proceeds through 5-exo-trig cyclization and delivers the products selectively with the E configuration of the double bond in excellent yields. The one-pot synthesis of 2-arylidene-3-aryl-1-indanones involving in situ synthesis of both 2'-iodochalcones and N-tosylhydrazones has also been demonstrated.
Department of Chemistry, Indian Institute of Technology Madras , Chennai-600036, Tamil Nadu, India.
Dhanarajan
D
Arunprasath
Department of Chemistry, Indian Institute of Technology Madras , Chennai-600036, Tamil Nadu, India.
Pandi
P
Muthupandi
Department of Chemistry, Indian Institute of Technology Madras , Chennai-600036, Tamil Nadu, India.
Govindasamy
G
Sekar