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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.