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Palladium(II)-Catalyzed C-H Activation and C-C Coupling/Cyclization of Benzamidine and Terminal Alkynes Using an Internal Oxidant

Xu Zhang*, Xuefeng Xu, Yingke Wu, Zhiqiang Wang, Lintao Yu, Qiang Zhao, Fu Shi

*School of Chemistry and Pharmacony Engineering, Nanyang Normal University, Nanyang 473061, P. R. of China, Email: zhangxuedu126.com

X. Zhang, X. Xu, Y. Wu, Z. Wang, L. Yu, Q. Zhao, F. Shi, Synlett, 2015, 26, 1885-1889.

DOI: 10.1055/s-0034-1380220 (free Supporting Information)



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Abstract

An efficient palladium(II)-catalyzed C-C coupling/cyclization reaction by directed C-H activation of benzamidine and terminal alkynes enables a practical and high-yielding synthesis of quinolines, in which the C-N bond acts as an internal oxidant. When using benzamidine with an ortho-methyl substituent, a [1,5]-hydrogen migration followed by a Diels-Alder reaction with terminal alkynes take place.

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Key Words

C-H activation, internal oxidant, C-C bond coupling, terminal alkynes, quinolines


ID: J60-Y2015