Construction of C(sp2)−X (X = Br, Cl) Bonds through a Copper-Catalyzed Atom-Transfer Radical Process: Application for the 1,4-Difunctionalization of Isoquinolinium Salts

Qiu Sun, Yuan-Yuan Zhang, Jing Sun, Ying Han, Xiaodong Jia, and Chao-Guo Yan*

School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, China

ABSTRACT:A highly efficient Cu-catalyzed 1,4-difunctionalization of isoquinolinium salts was developed with ether and X− (X = Br, Cl) as the halogen source under mild conditions. This transformation involves the combination of oxidative coupling and copper-catalyzed halogen atom-transfer radical processes. This method not only provides an efficient way to prepare various substituted azaarenes but also achieves the selective construction of C(sp²)−X (X = Br, Cl) bonds from a halogen anion and nucleophilic carbon atom via a free-radicalprocess.

Org. Lett.2018,20, 987−990, IF = 6.579

文章链接：https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b03751