Issue 27, 2021

Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Abstract

Carborane maleimides were prepared in good yields through the thermal cyclization of maleamic acids prepared by the reaction of 3-amino-o-carborane with maleic or 3-bromomaleic anhydrides, respectively. The selective reactivity of synthesized maleimides towards S-nucleophiles was demonstrated. As a result a series of boronated thiosuccinimide- or thiomaleimide-substituted compounds including boron rich ones was obtained and fully characterized. Furthermore the opportunity of variation with substitution patterns may lead to the development of potential candidates for biological applications or the development of new materials.

Graphical abstract: Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

Supplementary files

Article information

Article type
Paper
Submitted
21 May 2021
Accepted
17 Jun 2021
First published
23 Jun 2021

New J. Chem., 2021,45, 12159-12167

Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions

V. A. Ol'shevskaya, V. M. Alpatova, A. V. Makarenkov, E. G. Kononova, A. F. Smol’yakov, A. S. Peregudov and E. G. Rys, New J. Chem., 2021, 45, 12159 DOI: 10.1039/D1NJ02499J

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