Chemical Communications p. 9757 - 9760 (2019)
Update date:2022-08-03
Topics: Allylation C-H Activation Alkene Coordination Recovery of Catalyst
Xu, Liangyao
Meng, Keke
Zhang, Jian
Sun, Yaling
Lu, Xiunan
Li, Tingyan
Jiang, Yan
Zhong, Guofu
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.
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