ID 113072
著者
大西, 崇裕 Tokushima University
Kawahara, Takayuki Tokushima University
キーワード
Isoalloxazine
Flavin
Environmentally benign
Oxygenation
Aerobic oxidation
資料タイプ
学術雑誌論文
抄録
Isoalloxazine ring systems are found in flavin cofactors in nature, and the simulation of their redox catalyses is an important task for developing sustainable catalytic oxidation reactions. Although 5- ethyl-4a-hydroxyisoalloxazines are among the most promising candidates as catalyst for such purposes, the use of them for laboratorial as well as industrial synthetic chemistry has so far been quite limited presumably due to the lack of their preparation methods readily, safely, and inexpensively available. In this communication, we introduce an environmentally benign and practical preparation of 5-ethyl-4a-hydroxy-3,7,8,10-tetramethylisoalloxazine (1EtOH) from 3,7,8,10-tetramethylisoalloxazine (1), in which conventional synthetic requirements, including (i) operations under inert conditions, (ii) risky or expensive chemicals, and (iii) isolation of labile intermediates, have all been dissolved. In addition, we have presented that 1EtOH could be an effective catalyst for Baeyer-Villiger oxidation as well as sulfoxidation with molecular oxygen (O2) as a terminal oxidant under suitable conditions, which is the first report on aerobic oxygenations catalyzed by 5-alkyl-4a-hydroxyisoalloxazines.
掲載誌名
European Journal of Organic Chemistry
ISSN
10990690
1434193X
cat書誌ID
AA11619885
AA1118165X
出版者
WILEY‐VCH
2019
8
開始ページ
1791
終了ページ
1795
発行日
2019-01-02
備考
論文本文は2020-01-02以降公開予定
権利情報
This is the peer-reviewed version of the following article: Oonishi, T. , Kawahara, T. , Arakawa, Y. , Minagawa, K. and Imada, Y. (2019), Greener Preparation of 5‐Ethyl‐4ahydroxyisoalloxazine and Its Use for Catalytic Aerobic Oxygenations. Eur. J. Org. Chem., 2019: 1791-1795, which has been published in final form at https://doi.org/10.1002/ejoc.201801865. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
EDB ID
出版社版DOI
出版社版URL
言語
eng
著者版フラグ
その他
部局
理工学系
教養教育院