Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine.
basic_science · Level V
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- Record sourced from PubMed, PMID 26601302.
- Also identified by DOI 10.1126/sciadv.1500656 and PMC identifier 4646816.
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Abstract
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.