Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine

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 involv...

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Published in:Science advances 2015-10, Vol.1 (9), p.e1500656-e1500656
Main Authors: Wu, Kun, Huang, Zhiliang, Qi, Xiaotian, Li, Yingzi, Zhang, Guanghui, Liu, Chao, Yi, Hong, Meng, Lingkui, Bunel, Emilio E, Miller, Jeffrey T, Pao, Chih-Wen, Lee, Jyh-Fu, Lan, Yu, Lei, Aiwen
Format: Article
Language:English
Subjects:
Aerobic Oxidative Coupling
C-N Bond Formation
Copper-Catalyzed
DFT Calculations
EPR
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Organic Chemistry
SciAdv r-articles
XAFS
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Summary: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.
ISSN:2375-2548
2375-2548
DOI:10.1126/sciadv.1500656