Rh^III-Catalyzed [4 + 1] Annulations of 2‑Hydroxy- and 2‑Aminobenzaldehydes with Allenes: A Simple Method toward 3‑Coumaranones and 3-Indolinones

Abstract

A novel method for the regio- and stereoselective synthesis of substituted 3-coumaranones from salicylaldehydes and allenes using a rhodium­(III) catalyst has been developed. This procedure gives access to new 2-vinyl-substituted 3-coumaranone compounds. The method involves a Rh^III-catalyzed aldehyde C–H activation and annulation reactions. Moreover, this Rh^III-catalyzed [4 + 1] annulation reaction has been applied to 2-aminobenzaldehydes to afford 2,2-disubstituted 3-indolinones