ipso-Nitration of Arylboronic Acids with Chlorotrimethylsilane-Nitrate Salts

G. K. Surya Prakash,* Chiradeep Panja, Thomas Mathew, Vijayalakshmi Surampudi, Nicos A. Petasi, and George A. Olah

*Loker Hydrocarbon Research Institute and Department of Chemistry, UniVersity of Southern California, Los Angeles, California 90089-1661, Email: gprakashusc.edu

G. K. S. Prakash, C. Panja, T. Mathew, V. Surampudi, N. A. Petasi, G. A. Olah, Org. Lett., 2004, 6, 2205-2207.

DOI: 10.1021/ol0493249

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Abstract

A mixture of nitrate salt and chlorotrimethylsilane is an efficient, convenient, and regioselective nitrating agent for the ipso-nitration of arylboronic acids to produce the corresponding nitroarenes in moderate to excellent yields.

see article for more examples

proposed mechanism

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Mild Preparation of Haloarenes by Ipso-Substitution of Arylboronic Acids with N-Halosuccinimides

C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett, 1998, 141-142.

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Key Words

Nitration, Arylboronic acids, Ipso-substitution

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ID: J54-Y2004-2420