Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine
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.
- Authors:
-
[1];
[1];
- 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
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- 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
- OSTI Identifier:
- 1625948
- Grant/Contract Number:
- AC02-06CH11357
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Science Advances
- Additional Journal Information:
- Journal Volume: 1; Journal Issue: 9; Journal ID: ISSN 2375-2548
- Publisher:
- AAAS
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Copper-Catalyzed; Aerobic Oxidative Coupling; C-N Bond Formation; EPR; XAFS; DFT Calculations
Citation Formats
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, and Lei, Aiwen. Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine. United States: N. p., 2015.
Web. doi:10.1126/sciadv.1500656.
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. Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine. United States. https://doi.org/10.1126/sciadv.1500656
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, and Lei, Aiwen. Fri .
"Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine". United States. https://doi.org/10.1126/sciadv.1500656. https://www.osti.gov/servlets/purl/1625948.
@article{osti_1625948,
title = {Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine},
author = {Wu, Kun and Huang, Zhiliang and Qi, Xiaotian and Li, Yingzi and Zhang, Guanghui and Liu, Chao and Yi, Hong and Meng, Lingkui and Bunel, Emilio E. and Miller, Jeffrey T. and Pao, Chih-Wen and Lee, Jyh-Fu and Lan, Yu and Lei, Aiwen},
abstractNote = {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.},
doi = {10.1126/sciadv.1500656},
journal = {Science Advances},
number = 9,
volume = 1,
place = {United States},
year = {Fri Oct 09 00:00:00 EDT 2015},
month = {Fri Oct 09 00:00:00 EDT 2015}
}
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Enantioselective Direct-Addition of Terminal Alkynes to Imines Catalyzed by Copper(I)pybox Complex in Water and in Toluene
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Highly Efficient Copper-Catalyzed Nitro-Mannich Type Reaction: Cross-Dehydrogenative-Coupling between sp 3 C−H Bond and sp 3 C−H Bond
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Copper-Catalyzed Aerobic Oxidative Amidation of Terminal Alkynes: Efficient Synthesis of Ynamides
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Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C–H Oxidation
journal, June 2013
- Suess, Alison M.; Ertem, Mehmed Z.; Cramer, Christopher J.
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Cu-Catalyzed Esterification Reaction via Aerobic Oxygenation and C–C Bond Cleavage: An Approach to α-Ketoesters
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Simple Catalytic Mechanism for the Direct Coupling of α-Carbonyls with Functionalized Amines: A One-Step Synthesis of Plavix
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- Journal of the American Chemical Society, Vol. 135, Issue 43
Direct Observation of Reduction of Cu(II) to Cu(I) by Terminal Alkynes
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Cu(II)–Cu(I) Synergistic Cooperation to Lead the Alkyne C–H Activation
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- Journal of the American Chemical Society, Vol. 136, Issue 48
Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives
journal, December 2002
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- Journal of Medicinal Chemistry, Vol. 45, Issue 25
Discovery of Novel Potent and Highly Selective Glycogen Synthase Kinase-3β (GSK3β) Inhibitors for Alzheimer’s Disease: Design, Synthesis, and Characterization of Pyrazines
journal, April 2012
- Berg, Stefan; Bergh, Margareta; Hellberg, Sven
- Journal of Medicinal Chemistry, Vol. 55, Issue 21
Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase: Structure−Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins
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Application of N-phenyltrifluoromethanesulfonamides to the synthesis of pyrazines
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Iron-catalyzed Cross-Coupling of Electron-Deficient Heterocycles and Quinone with Organoboron Species via Innate C–H Functionalization: Application in Total Synthesis of Pyrazine Alkaloid Botryllazine A
journal, February 2013
- Singh, Parvinder Pal; Aithagani, Sravan Kumar; Yadav, Mahipal
- The Journal of Organic Chemistry, Vol. 78, Issue 6
General and Efficient Copper-Catalyzed Amidation of Saturated C−H Bonds Using N -Halosuccinimides as the Oxidants
journal, August 2008
- Liu, Xiaowei; Zhang, Yongming; Wang, Long
- The Journal of Organic Chemistry, Vol. 73, Issue 16
CuI/BF 3 ·Et 2 O Cocatalyzed Aerobic Dehydrogenative Reactions of Ketones with Benzylamines: Facile Synthesis of Substituted Imidazoles
journal, November 2012
- Cai, Zhong-Jian; Wang, Shun-Yi; Ji, Shun-Jun
- Organic Letters, Vol. 14, Issue 23
Potassium t -Butoxide Alone Can Promote the Biaryl Coupling of Electron-Deficient Nitrogen Heterocycles and Haloarenes
journal, October 2008
- Yanagisawa, Shuichi; Ueda, Kirika; Taniguchi, Tadashi
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Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant
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Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant
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Electrochemical oxidation synergizing with Brønsted-acid catalysis leads to [4 + 2] annulation for the synthesis of pyrazines
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