Development og highly reactive halogenation reaction using sulfur compound and its applications

2022 Fiscal Year Final Research Report

• Project/Area Number: 18K05132
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Kindai University
• Principal Investigator: Maegawa Tomohiro 近畿大学, 薬学部, 教授 (40363890)
• Project Period (FY): 2018-04-01 – 2023-03-31
• Keywords: ハロゲン化 / 硫黄化合物 / 活性化 / N-ハロスクシンイミド

Outline of Final Research Achievements

In this study, we found that the reactivity of N-bromosuccinimide, whose reactivity was conventionally low, is greatly improved by using phenylthiotrimethylsilane, a sulfur compound, with N-bromosuccinimide.
(1) Bromination and chlorination of relatively electron poor aromatic rings, which cannot proceed with N-bromosuccinimide alone, are efficiently promoted by the addition of phenylthiotrimethylsilane. (2) We found that direct esterification from cyclic acetals proceeded by using these reagents combination. (3) By using this reagent combination, we found that radical reactions proceed at room temperature.

Free Research Field

有機反応化学

Academic Significance and Societal Importance of the Research Achievements

臭素や塩素といったハロゲン化合物は様々な分野で有用な化合物として用いられており、その合成法も多く開発されています。しかし、反応性の高い反応剤は様々な化合物をハロゲン化することができますが、反面、取り扱いがむずかしいといった問題があります。今回開発した方法は、反応性は低いものの取り扱いが容易な試薬に対して、硫黄化合物を添加することでその反応性を大きく向上させることに成功しました。