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Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine. 2015
Kun Wu, and
Zhiliang Huang, and
Xiaotian Qi, and
Yingzi Li, and
Guanghui Zhang, and
Chao Liu, and
Hong Yi, and
Lingkui Meng, and
Emilio E Bunel, and
Jeffrey T Miller, and
Chih-Wen Pao, and
Jyh-Fu Lee, and
Yu Lan, and
Aiwen Lei
College of Chemistry and Molecular Sciences, Institute for Advanced Studies, Wuhan University, Wuhan 430072, China.
Copper-catalyzed aerobic oxidative C-H/N-H coupling between simple ketones and diamines was developed toward the synthesis of a variety of pyrazines. Various substituted ketones were compatible for this transformation. Preliminary mechanistic investigations indicated that radical species were involved. X-ray absorption fine structure experiments elucidated that the Cu(II) species 5 coordinated by two N atoms at a distance of 2.04 Å and two O atoms at a shorter distance of 1.98 Å was a reactive one for this aerobic oxidative coupling reaction. Density functional theory calculations suggested that the intramolecular coupling of cationic radicals was favorable in this transformation.
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