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

Sébastien Redon; Anne Roly Obah Kosso; Julie Broggi; Patrice Vanelle

doi:10.1055/s-0039-1690013

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(19): 3758-3764
DOI: 10.1055/s-0039-1690013

paper

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

Sébastien Redon ∗

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

,

Julie Broggi

,

Patrice Vanelle ∗

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

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Abstract

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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.

Key words

selenocyanate - arylboronic acid - selenium dioxide - malononitrile - diaryldiselenide

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