BF3·OEt2 catalyzed decarbonylative arylation/C-H functionalization of diazoamides with arylaldehydes: synthesis of substituted 3-aryloxindoles.

Abstract

A metal-free BF3·OEt2 catalyzed direct decarbonylative arylation of diazoamides with readily accessible aryl aldehydes under an open-air atmosphere was developed to afford 3-aryloxindoles via 1,2-aryl migration with high selectivity. The reaction offers an efficient pathway for 3-arylation of diazoamides under relatively mild conditions, which shows a high level of functional group tolerance of both electron-donating and electron-withdrawing groups with a broad substrate scope. 3-Aryloxindoles were also obtained by a substituent-controlled chemo- and site-selective C-H bond functionalization of unprotected salicylaldehyde derivatives.