Iridium-catalyzed alkenyl C–H allylation using conjugated dienes. Issue 66 (29th July 2019) - Xu, Liangyao
Abstract : An iridium-catalyzed olefinic C–H allylation of acrylamides with conjugated dienes was developed, providing an atom economic synthesis of skipped 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.