論文 2017


▼論文発表
酸塩基複合化学に立脚する高機能触媒の創製
石原一彰
有機合成化学協会誌 2017, 75(2), 98-110.
DOI: http://doi.org/10.5059/yukigoseikyokaishi.75.98
J-STAGE公開日 20170406
https://www.jstage.jst.go.jp/…/75/2/75_98/_article/-char/ja/

The acid-base combination chemistry is one of the most reliable concepts for designing high performance catalysts. Acid-base combined catalysts can be classified into two types, ion pair catalysts (type A) and acid-base cooperative catalysts (type B). Type A can be subclassified into acidic/basic/neutral salt catalysts (types A1/A2/A3). Type B can be subclassified into conjugationally noninteractive/interactive acid-base catalysts (types B1/B2). Tailor-made multi-selective catalysts can also be designed based on the acid-base combination chemistry. Our recent progress has been described here.

▼論文発表
4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols
Muhammet Uyanik, Tatsuya Mutsuga and Kazuaki Ishihara*
Angew. Chem. Int. Ed. 2017, 56(14), 3956–3960.
Version of Record online: 21 FEB 2017 | DOI: 10.1002/anie.201612463
http://onlinelibrary.wiley.com/doi/10.1002/anie.201612463/full

A site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers, catalyzed by 4,5-dimethyl-2-iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinilene C methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of a trialkylsilylmethyl substituent at the 2-position of phenols. The corresponding 1,2-quinols could be transformed into various useful structural motifs by [4+2] cycloaddition cascade reactions.

Ammonium Hypoiodite-Catalyzed Peroxidative Dearomatization of Phenols
Muhammet Uyanik, Kohei Nishioka, and Kazuaki Ishihara*
Heterocycles, 2017, 95(2), 1132–1147 (Masakatsu Shibasaki's Special Issue).
Published online: 31st January, 2017
DOI: 10.3987/COM-16-S(S)84

https://www.heterocycles.jp/newlibrary/payments/form/25006/PDF

Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.

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Postdoctoral and graduate students is being recruited.In our laboratory will be accepted at any time undergraduate, graduate student visits to laboratories.Those who wish, please contact us by e-mail to Professor Ishihara.

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ISHIHARA GROUP

名古屋大学

大学院工学研究科 有機・高分子化学専攻(工学部 化学生命工学科)
有機化学講座

触媒有機合成学研究グループ

〒464-8603 名古屋市千種区不老町

B2-3(611)

 

Laboratory of Catalysis in Organic Synthesis, Research Group of Molecular Chemistry, Graduate Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering (Undergraduate Department of Chemistry and Biotechnology, School of Engineering), Nagoya University

B2-3(611), Furo-cho, Chikusa, Nagoya 464-8603, Japan