Highly Stereoselective Synthesis of Imine‐Containing Dibenzo[b, d]azepines by a Palladium(II)‐Catalyzed [5+2] Oxidative Annulation of o‐Arylanilines with Alkynes. Issue 51 (2nd November 2015)

• Record Type: Journal Article
• Authors: Zuo, Zhijun; Liu, Jingjing; Nan, Jiang; Fan, Liangxin; Sun, Wei; Wang, Yaoyu; Luan, Xinjun
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 51(2015)
• Page Start: 15385
• Page End: 15389
• Publication Date: 2015-11-02
• Subjects: annulations -- arenes -- CH activation -- heterocycles -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201508850
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A novel palladium(II)‐catalyzed [5+2] oxidative annulation of readily available o ‐arylanilines with alkynes has been developed for building a seven‐membered N‐heterocyclic architecture containing a biaryl linkage. This method is applicable to a wide range of unprotected o ‐arylanilines and internal alkynes, and results in the chemoselective preparation of imine‐containing dibenzo[ b, d ]azepines in high yields with excellent diastereoselectivity with respect to the two types of stereogenic elements. Abstract : Link up : The title reaction has been developed for building a seven‐membered N‐heterocyclic architecture containing a biaryl linkage. This method is applicable to a wide range of unprotected o ‐arylanilines and internal alkynes, and results in the chemoselective preparation of imine‐containing dibenzo[ b, d ]azepines in high yields with excellent diastereoselectivity with regard to the two types of stereogenic elements.