Synthesis 2002(10): 1454-1458
DOI: 10.1055/s-2002-33110
PSP
© Georg Thieme Verlag Stuttgart · New York

An Efficient Procedure for the Synthesis of ortho-Trialkylsilylaryl Triflates: Easy Access to Precursors of Functionalized Arynes

Diego Peña, Agustín Cobas, Dolores Pérez*, Enrique Guitián*
Departamento de Química Orgánica, Universidad de Santiago de Compostela and Unidad Asociada al CSIC, 15706 Santiago de Compostela, Spain
Fax: +34(981)591014; e-Mail: [email protected];
Further Information

Publication History

Received 3 April 2002
Publication Date:
01 August 2002 (online)

Abstract

o-Trialkylsilylaryl triflates, which are useful aryne precursors, are prepared from o-bromophenols by an efficient, one-pot procedure involving O-silylation, metal-halogen exchange, O- to C-silyl migration, and entrapment of the phenoxide with triflic anhydride.

    References

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    Obtained by the reaction of 2-bromoresorcinol with K2CO3 and pent-3-ynyl p-toluenesulfonate.

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Now commercially available from Sigma-Aldrich.