原创力文档synthesis of heteroaromatic compounds by oxidative aromatization using an activated carbonmolecular oxygen systemheteroaromatic化合物的合成氧化芳构化使用激活carbonmolecular氧气系统.pdfVIP
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synthesis of heteroaromatic compounds by oxidative aromatization using an activated carbonmolecular oxygen systemheteroaromatic化合物的合成氧化芳构化使用激活carbonmolecular氧气系统
Molecules 2009, 14, 3073-3093; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Review
Synthesis of Heteroaromatic Compounds by Oxidative
Aromatization Using an Activated Carbon/Molecular
Oxygen System
Yuka Kawashita and Masahiko Hayashi *
Department of Chemistry, Graduate School of Science, Kobe University, Kobe 657-8501, Japan;
E-mail: mhayashi@kobe-u.ac.jp (Y.K.)
* Author to whom correspondence should be addressed; E-mail: mhayashi@kobe-u.ac.jp
Received: 6 July 2009; in revised form: 31 July 2009 / Accepted: 10 August 2009 /
Published: 14 August 2009
Abstract: A variety of heteroaromatic compounds, such as substituted pyridines,
pyrazoles, indoles, 2-substituted imidazoles, 2-substituted imidazoles, 2-arylbenzazoles
and pyrimidin-2(1H)-ones are synthesized by oxidative aromatization using the activated
carbon and molecular oxygen system. Mechanistic study focused on the role of activated
carbon in the synthesis of 2-arylbenzazoles is also discussed. In the final section, we will
disclose the efficient synthesis of substituted 9,10-anthracenes via oxidative aromatization.
Keywords: oxidation; aromatization; heteroaromatic compound; activated carbon
1. Introduction
1.1. Activated carbon—O oxidation system; How we discovered it!
2
The oxidation of alcohols to carbonyl compounds is one of the most fundamental reactions in
organic synthesis [1]. In 1999, we first reported a Pd/C—ethylene system for the oxidation of benzylic
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