Issue 20, 2023

Efficient oxyselenation and aminoselenation utilizing a selenenyl iodide based on the characteristic thermodynamics of its reaction with olefins

Abstract

In contrast to selenenyl chlorides (RSeCl) or bromides (RSeBr), which are widely used in organic synthesis, the reactivity of selenenyl iodides (RSeI) remains largely unelucidated due to their instability. The thermodynamics of the reaction of RSeI with an olefin were investigated utilizing an isolable selenenyl iodide, BpqSeI, and the ΔH° value of its reaction with cyclohexene suggested analogous features of RSeI and I2 as electrophiles for their addition to olefins. Based on such characteristic thermodynamics, the efficient selenofunctionalization of olefins with external oxygen or nitrogen nucleophiles using BpqSeI was developed. In the presence of an appropriate additive, such as N-iodosuccinimide, various alcohols, a carboxylic acid, and aromatic amines were smoothly introduced into olefins to give the corresponding β-oxyselenides and β-aminoselenides in moderate to high yields.

Graphical abstract: Efficient oxyselenation and aminoselenation utilizing a selenenyl iodide based on the characteristic thermodynamics of its reaction with olefins

Supplementary files

Article information

Article type
Paper
Submitted
29 дек 2022
Accepted
28 мар 2023
First published
29 мар 2023

New J. Chem., 2023,47, 9569-9574

Efficient oxyselenation and aminoselenation utilizing a selenenyl iodide based on the characteristic thermodynamics of its reaction with olefins

S. Kuwano, E. Takahashi, J. Kikushima, S. Sase and K. Goto, New J. Chem., 2023, 47, 9569 DOI: 10.1039/D2NJ06346H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements