Abstract
Heterocyclic arynes hold much promise for applications in modern
synthetic chemistry. One particular class of hetarynes is those
derived from the indole heterocycle (i.e., indolynes). Indolynes
can be generated under mild fluoride-based reaction conditions using
silyltriflate precursors. Indolyne-trapping experiments provide
access to benzenoid-substituted indoles in a controlled manner with
synthetically useful yields. Regioselectivities can be predicted
prior to experiments using simple calculations, ultimately allowing
for the modulation of selectivities by careful design. This strategy
has enabled a concise synthesis of indolactam V.
Key words
arynes - indoles - regioselectivity - total
synthesis - indolynes
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