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Synthesis 2023; 55(11): 1764-1769
DOI: 10.1055/a-1988-6052
paper
Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Palladium-Catalyzed Denitrogenative Cross-Coupling of Silicon-Masked, Aryl-Substituted Diazenes and Aryl Bromides

Lucie Finck  ‡
,
Sarah Dabrowski  ‡
,
Martin Oestreich  ∗
This research was supported by the Deutsche Forschungsgemeinschaft (Oe 249/23-1). M.O. is indebted to the Einstein Stiftung Berlin for an endowed professorship.
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Abstract

A denitrogenative palladium-catalyzed C(sp2)–C(sp2) cross-coupling of aryl-substituted diazenes capped with a trimethylsilyl group and functionalized aryl bromides is reported. A PEPPSI™ catalyst in the presence of NaOt-Bu enables the activation of the N-aryl-N′-silyldiazene pronucleophile with concomitant loss of dinitrogen and subsequent coupling of the in-situ-formed aryl nucleophile. By this, biaryl compounds bearing a variety of substituents can be prepared.

Key words

biaryls - chemoselectivity - cross-coupling - denitrogenation - diazene - palladium - silicon

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1988-6052.
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Publication History

Received: 11 November 2022

Accepted: 28 November 2022

Accepted Manuscript online:
28 November 2022

Article published online:
03 January 2023

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