Cobalt(II)‐Catalyzed [5+2] C−H Annulation of  o ‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[ b , d ]azepines | Zendy

Ling Fei | Zendy; Xie Zhen | Zendy; Chen Jiachen | Zendy; Ai Chongren | Zendy; Shen Haiwei | Zendy; Wang Ze | Zendy; Yi Xiao | Zendy; Zhong Weihui | Zendy

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

Author(s) -

Ling Fei,

Xie Zhen,

Chen Jiachen,

Ai Chongren,

Shen Haiwei,

Wang Ze,

Yi Xiao,

Zhong Weihui

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201900261

Subject(s) - azepine , chemistry , annulation , catalysis , regioselectivity , imine , substrate (aquarium) , alkyne , cobalt , combinatorial chemistry , manganese , medicinal chemistry , stereochemistry , organic chemistry , oceanography , geology

The first example of CoCl 2 ‐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.

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