Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b, d]azepines. Issue 13 (9th May 2019)

• Record Type: Journal Article
• Authors: Ling, Fei; Xie, Zhen; Chen, Jiachen; Ai, Chongren; Shen, Haiwei; Wang, Ze; Yi, Xiao; Zhong, Weihui
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 13(2019)
• Page Start: 3094
• Page End: 3101
• Publication Date: 2019-05-09
• Subjects: C−H activation -- cobalt -- [5+2] annulation -- dibenzo-[b, d]azepine -- picolinamide; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900261
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The first example of CoCl2 ‐catalyzed formal [5+2] oxidative annulation of o ‐arylanilines with alkynes was developed, giving access to various important imine‐containing dibenzo‐[ b, d ]azepine scaffolds through sequential C−C/C−N bond formation. The reaction employs catalytic amount of manganese and oxygen as cooxidants, and features a broad substrate scope. Preliminary mechanistic studies suggested that C−H activation is involved in the rate‐determining step. Moreover, both internal and terminal alkynes are well tolerated in this transformation. Besides, a regioselective migratory insertion was observed when using terminal alkynes as substrates. Abstract :