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Aryne Trifunctionalization Enabled by 3‑Silylaryne as a 1,2‑Benzdiyne Equivalent
An
unprecedented aryne 1,2,3-trifunctionalization protocol from
2,6-bisÂ(silyl)Âaryl triflates was developed under transition-metal-free
conditions. The reaction of generated 3-silylaryne with both pyridine <i>N</i>-oxide and <i>N</i>-hydroxylamide afforded <i>o</i>-silyl triflate/tosylate in a one-pot transformation, allowing
the formation of 2,3-aryne precursors with various vicinal pyridinyl/amido
substituents. These pyridinyl-substituted 2,3-aryne intermediates
exhibit a broad scope of reactivity with diverse arynophiles in good
yields and high selectivity