Journal
ORGANIC LETTERS
Volume 23, Issue 6, Pages 2189-2193Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00342
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Funding
- National Institutes of General Medical Sciences [R35 GM127097]
- National Science Foundation [CHE 1665389, MRI 1229400]
- National Institutes of Health Shared Instrumentation Grant program [S10OD011952]
- Cancer Center Support Grant [CA-77598]
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This study reports a successful reaction of benzynes generated by hexadehydro-Diels-Alder reaction with coumarin to produce phenanthrene derivatives, highlighting the reactivity difference between 2-pyrone and coumarin.
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.
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