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Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes

Balaji V. Rokade and Kandikere Ramaiah Prabhu*

*Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, Email: prabhuorgchem.iisc.ernet.in

B. V. Rokade, J. R. Prabhu, J. Org. Chem., 2012, 77, 5364-5370.

DOI: 10.1021/jo3008258 (free Supporting Information)


Abstract

The Schmidt reaction of aldehydes with NaN3 furnishes the corresponding nitriles in near quantitative yields in the presence of TfOH and tolerates various electron-withdrawing and electron-donating substituents. Formanilides,  common side products, are not observed. The reaction is easily scalable, high yielding, and nearly instantaneous.

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proposed mechanism



Key Words

Schmidt Reaction, Nitriles


ID: J42-Y2012-1910