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Updated: May 23, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Preparation and characterization of aryl or heteroaryl(3-indolyl)methylium o-benzenedisulfonimides
Margherita Barbero1, Silvano Cadamuro, Fabrizio Cauda
1Dipartimento di Chimica, Università di Torino, Via P. Giuria 7, 10125 Torino, Italy. margherita.barbero@unito.it
Abstract:
An initial study has been accomplished into the synthetic feasibility of the preparation of diarylcarbenium salt via the direct coupling of aryl (or heteroaryl) aldehydes and arenes (or heteroaryl analogues) in the presence of a strong organic Brønsted acid. A number of stabilized aryl or heteroaryl(3-indolyl)carbenium ions, never previously prepared in the solid state, have been isolated in excellent yields as highly stable o-benzenedisulfonimide salts and have been fully characterized. Their purity has been proven by spectroscopic methods and chemical reduction with NaBH(4). An X-ray crystal structure analysis has been performed on one of the products: an azafulvenium species was shown to be the exclusive structure in the solid state.
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