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Rh(II)-catalyzed intermolecular carboamination of pyridines via double Csp2–H bond activations

Luo Zhongfeng,Jiang Jingxing,Zou Lifang,Zhou Xiaoyu,Liu Junshan,Ke Zhuofeng,Chen Fengjuan,Jiang Huanfeng,Zeng Wei

We disclose the development of the Rh-catalyzed amine-directed remote 5,6-carboamination protocol of pyridines via dual Csp 2 –H functionalizations. A variety of readily available 2-aminopyridines and 1,2,3-triazoles are allowed for coupling cyclization to access polyfunctionalized azaindoles. Mechanistic studies including DFT calculations unveil that relay carbenoid-electrophilic addition to pyridines and the sequential pyridyl Csp 2 –H amination are involved in this transformation. The post-synthetic utility of this methodology is showcased by versatile and site-selective modification of azaindoles.