Introduction of Molecular Complexity via the Cross-Coupling of Lithium 1,4-Dioxene with Aryl Bromides

Paco Visser, Ben L Feringa*

*Corresponding author voor dit werk

OnderzoeksoutputAcademicpeer review

1 Citaat (Scopus)
34 Downloads (Pure)

Samenvatting

The synthetic potential of substituted 1,4-dioxenes is well recognised, although the chemistry of 2-aryl-1,4-dioxenes is relatively unexplored. Their transition metal-catalysed synthesis has been limited to Stille-type cross-coupling chemistry, typically showing long reaction times, or proceeding at high reaction temperatures. Here we present a facile and general methodology for the cross-coupling of aryl bromides with lithium 1,4-dioxene, affording a range of 2-aryl-1,4-dioxenes in generally good yields. We highlight the synthetic applicability of this transformation at multigram scale, and demonstrate the versatility of the products by conversion of the dioxene units to various carbonyl-based functionalities. Additionally, we present a concise two-step synthesis of an arylated analogue to a known 1,4-dioxene-based antifungal agent.
Originele taal-2English
Artikelnummere202402351
Aantal pagina's8
TijdschriftChemistry – A European Journal
Volume30
Nummer van het tijdschrift61
Vroegere onlinedatum16-okt.-2024
DOI's
StatusPublished - 4-nov.-2024

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