ID 113072
Author
Oonishi, Takahiro Tokushima University
Kawahara, Takayuki Tokushima University
Keywords
Isoalloxazine
Flavin
Environmentally benign
Oxygenation
Aerobic oxidation
Content Type
Journal Article
Description
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.
Journal Title
European Journal of Organic Chemistry
ISSN
10990690
1434193X
NCID
AA11619885
AA1118165X
Publisher
WILEY‐VCH
Volume
2019
Issue
8
Start Page
1791
End Page
1795
Published Date
2019-01-02
Remark
論文本文は2020-01-02以降公開予定
Rights
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
DOI (Published Version)
URL ( Publisher's Version )
language
eng
TextVersion
その他
departments
Science and Technology
Liberal Arts and Sciences