Iridium-catalyzed alkenyl C–H allylation using conjugated dienes

Abstract

An iridium-catalyzed C–H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand- and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF₃. The utility of this protocol is also demonstrated by a preparative scale, as well as C–H functionalization of artemisic amide. Furthermore, NH-Ts amide was efficiently removed by methylation and hydrolysis procedures to provide 1,4-dienoic acid.