Synthesis 2019; 51(19): 3758-3764
DOI: 10.1055/s-0039-1690013
paper
© Georg Thieme Verlag Stuttgart · New York

Metal-Free ipso-Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide

Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, 13385 Marseille Cedex 5, France   Email: sebastien.redon@univ-amu.fr   Email: patrice.vanelle@univ-amu.fr
,
Anne Roly Obah Kosso
,
,
Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, 13385 Marseille Cedex 5, France   Email: sebastien.redon@univ-amu.fr   Email: patrice.vanelle@univ-amu.fr
› Author Affiliations
Aix-Marseille Université and the Centre National de la Recherche Scientifique (CNRS) are gratefully acknowledged for financial support.
Further Information

Publication History

Received: 07 June 2019

Accepted after revision: 16 July 2019

Publication Date:
01 August 2019 (online)


Abstract

The first ipso-selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.

Supporting Information

 
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