Abstract
Although the parent 2-pyrone is known to react with simple o-benzynes to produce naphthalene derivatives, there appear to be no examples of the successful reaction of coumarin, a benzo-annulated 2-pyrone analogue, with an aryne. We report such a process here using benzynes generated by the hexadehydro-Diels-Alder reaction to produce phenanthrene derivatives (i.e., benzo-annulated naphthalenes). Density functional theory computations were used to help understand the difference in reactivity between 2-pyrone and the slower trapping agent, coumarin. Finally, the reaction of o-benzyne itself [from o-(trimethylsilyl)phenyl triflate and CsF] with coumarin was shown to be viable, although slow.
Original language | English (US) |
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Pages (from-to) | 2189-2193 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 23 |
Issue number | 6 |
DOIs | |
State | Published - Mar 19 2021 |
Bibliographical note
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