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Org Lett. 2012 Apr 20;14(8):2022-5. doi: 10.1021/ol300529j. Epub 2012 Apr 11.

Design and application of new imidazolylsulfonate-based benzyne precursor: an efficient triflate alternative.

Organic letters

Szabolcs Kovács, Ádám I Csincsi, Tibor Zs Nagy, Sándor Boros, Géza Timári, Zoltán Novák

Affiliations

  1. Institute of Chemistry, Eötvös Loránd University, Pázmány Péter stny 1/a, H-1117 Budapest, Hungary.

PMID: 22494252 DOI: 10.1021/ol300529j

Abstract

Several o-(trimethylsilyl)aryl imidazolylsulfonates were synthesized in a simple process and successfully applied in cycloadditions involving benzyne intermediates. The precursor offers an efficient alternative for generating benzynes compared to widely used ortho TMS triflates under similar reaction conditions. With the utilization of this new precursor, the formation of potentially genotoxic trifluoromethanesulfonate side product is eliminated. The applicability of the new benzyne precursor was demonstrated in different types of cycloaddition reactions to prepare heterocyclic molecules.

© 2012 American Chemical Society

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