Chelation-assisted iridium-catalyzed hydroalkenylation and hydroarylation/cyclization with conjugated trienes.

Abstract

Iridium-catalyzed hydroalkenylation of conjugated trienes by chelation-assisted alkenyl C-H activation of acrylamides has been demonstrated to produce 1,4,6-trienes atom efficiently with excellent regio- and E/Z selectivities. In contrast, the reaction of benzamides and 1,3,5-trienes proceeds by a tandem hydroarylation of the trienes and cyclization via intramolecular 1,2-addition, providing valuable trans-tetrahydroisoquinolinone derivatives. A broad range of aromatic and aliphatic 1,3,5-trienes bearing various functionalities were compatible to deliver target products with high yields and E/Z selectivity. The successful gram-scale preparation and selective hydrogenation to give the alkylation product further demonstrates the practicability of this protocol to potential applications.