An unprecedented synthesis of novel 3-azido indoles has been developed using I2 and NaN3 in high yields and excellent regioselectivity. The reaction proceeds under metal-free conditions at room temperature. Essentially, an umpolung in reactivity at the C-3 position of indole has been achieved by the activation of indoles with I2.
The directed C–H alkynylation
of 2-(hetero)arylquinazolin-4-ones
has been explored with the ethynylbenziodoxolone reagent TIPS-EBX
employing an Ir(III) catalyst. Complementary conditions for either
monoalkynylation or dialkynylation have been developed. Also demonstrated
is the broad scope of this reaction and the compatibility of various
functional groups such as −F, −Cl, −Br, −CF3, −OMe, −NO2, and alkyl, etc.
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