2016
DOI: 10.1002/ejoc.201600531
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Iron‐Catalyzed Arene Prenylation

Abstract: The syntheses of prenylated arenes and 2,2‐dimethylchromans using a Friedel–Crafts‐type coupling between activated arenes and isoprene is reported. A combination of catalytic amounts of FeCl3 and AgBF4 promotes a regioselective prenylation event followed by a cyclization to form a 2,2‐dimethylchroman structure. The method avoids isoprene polymerization and allows the facile late‐stage derivatization of biologically active motifs.

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Cited by 15 publications
(1 citation statement)
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“…Importantly, the transition metal route also proceeds to yield the anti-Markovnikov products. Our laboratory’s interest in atom-efficient functionalizations of π-systems prompted us to explore a strategy to generate diarylmethines through the hydroarylation of styrene derivatives. To address the shortcomings of previous reports, we searched for a low-cost, mild method for the hydroarylation of styrene derivatives.…”
mentioning
confidence: 99%
“…Importantly, the transition metal route also proceeds to yield the anti-Markovnikov products. Our laboratory’s interest in atom-efficient functionalizations of π-systems prompted us to explore a strategy to generate diarylmethines through the hydroarylation of styrene derivatives. To address the shortcomings of previous reports, we searched for a low-cost, mild method for the hydroarylation of styrene derivatives.…”
mentioning
confidence: 99%