Design and Application of New Imidazolylsulfonate-Based Benzyne Precursor: An Efficient Triflate Alternative, Szabolcs Kovács, Ádám I. Csincsi, Tibor Zs. Nagy, Sándor Boros, Géza Timári, Zoltán Novák, Org. Lett. 2012, 14, 2022-2025. DOI: 10.1021/ol300529j | [Full Text Link] [Supp. Info Link]

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.