Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5 + 2] Annulation of o-Arylanilines with Dienes

• DOI: 10.1021/acs.orglett.7b00503
• Publication Date: 2017-03-15T14:56:30Z
• Authors: Lu Bai; Yan Wang; Yicong Ge; Jingjing Liu; Xinjun Luan
• Keywords: 01 natural sciences; 0104 chemical sciences

An efficient method for the construction of dibenzo[b,d]azepines containing two distinct stereogenic elements in a highly diastereoselective fashion is described. The key of the [5 + 2] reaction is to form a π-allylpalladium species through sequential C-H activation and regiospecific migratory insertion of the diene. This observation contrasts with the behavior of 1,2-alkenes that generally underwent direct alkenylation via β-hydride elimination.