Synthesis of 1,1-Disubstituted Indenes and Dihydronaphthalenes through C-C/C-C Bond-Forming Pd-Catalyzed Autotandem Reactions.

Abstract

A novel synthesis of 1,1-disubstituted 1H-indenes is described involving the Pd-catalyzed cascade reaction between o-bromophenyl-β-bromostyrenes and N-tosylhydrazones in a process comprising the consecutive formation of two Csp3-C bonds on the same carbon atom: the cross-coupling of the N-tosylhydrazone with the alkenyl bromide and the intramolecular Heck reaction on the newly formed double bond. A similar approach has been applied to the preparation of 1,1-disubstituted naphthalenes.