Pd(II)-Catalyzed ortho-C–H Olefination/Dearomatization of N‑Aryl Ureas: An Approach to Imine Derivatives
datasetposted on 02.03.2016 by Pingping Jiang, Yongbao Xu, Fuxing Sun, Xufei Liu, Feng Li, Renfu Yu, Yang Li, Qifeng Wang
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An unprecedented approach for the synthesis of imine derivatives was achieved via a Pd(II)-catalyzed dearomatization reaction of N-aryl ureas with internal alkynes. The corresponding spirocyclic imine derivatives were obtained with 20 examples in good to excellent yields. Mechanistic investigation indicated that an interesting 1,3-palladium migration process led to the α-regioselective dearomatization when 2-naphthyl ureas were used as the substrates. Fused ring products could also be obtained to further prove this migration process.