Design and Application of New Imidazolylsulfonate-Based Benzyne Precursor: An Efficient Triflate Alternative

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 reactio...

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Published inOrganic letters Vol. 14; no. 8; pp. 2022 - 2025
Main Authors Kovács, Szabolcs, Csincsi, Ádám I, Nagy, Tibor Zs, Boros, Sándor, Timári, Géza, Novák, Zoltán
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.04.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GENERAL-SYNTHESIS
INSERTION
ENANTIOSELECTIVE SYNTHESIS
CONCISE TOTAL-SYNTHESIS
CLICK CHEMISTRY
1,3-DIPOLAR CYCLOADDITION
ARYLATION
ARYNES
BOND
PALLADIUM-CATALYZED ANNULATION
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol300529j