Nitro-Assisted Brønsted Acid Catalysis: Application to a Challenging Catalytic Azidation

Marian Dryzhakov, Malik Hellal, Eléna Wolf, Florian C. Falk and Joseph Moran*

*ISIS & icFRC, Université de Strasbourg & CNRS, 8 allée Gaspard Monge, 67000 Strasbourg, France, Email: moranunistra.fr

M. Dryzhakov, M. Hellal, E. Wolf, F. C. Falk, J. Moran, J. Am. Chem. Soc., 2015, 137, 9555-9558.

DOI: 10.1021/jacs.5b06055

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Abstract

A cocatalytic effect of nitro compounds enables a B(C₆F₅)₃·H₂O catalyzed azidation of tertiary aliphatic alcohols with a broad range of substrates. Kinetic, electronic, and spectroscopic evidence suggests that higher order hydrogen-bonded aggregates of nitro compounds and acids are the kinetically competent Brønsted acid catalysts.

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Key Words

alkyl azides

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ID: J48-Y2015