Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine
- Wuhan Univ. (China). Institute for Advanced Studies, College of Chemistry and Molecular Sciences
- Wuhan Univ. (China). Institute for Advanced Studies, College of Chemistry and Molecular Sciences; Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Div.
- Chongqing Univ. (China). School of Chemistry and Chemical Engineering
- Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Div.
- National Synchrotron Radiation Research Center, Hsinchu (Taiwan)
- Wuhan Univ. (China). Institute for Advanced Studies, College of Chemistry and Molecular Sciences; Argonne National Lab. (ANL), Argonne, IL (United States). Chemical Sciences and Engineering Div.; Jiangxi Normal Univ., Nanchang (China). National Research Center for Carbohydrate Synthesis
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.
- Research Organization:
- Argonne National Laboratory (ANL), Argonne, IL (United States)
- Sponsoring Organization:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Natural Science Foundation of China (NSFC); Research Fund for the Doctoral Program of Higher Education of China; Program for Changjiang Scholars and Innovative Research Team in University; Ministry of Science and Technology of China
- Grant/Contract Number:
- AC02-06CH11357
- OSTI ID:
- 1625948
- Journal Information:
- Science Advances, Vol. 1, Issue 9; ISSN 2375-2548
- Publisher:
- AAASCopyright Statement
- Country of Publication:
- United States
- Language:
- English
Cited by: 23 works
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Web of Science
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