4-Aryl- and 4-vinyl-2,2-dialkyl-3-chromenes were prepared from tertiary 3-(o-bromoplienyl)propynols and aryl iodides or vinyl triflates through a one-pot process, which involves the addition of t-BuONa, dppf and, where appropriate, fresh Pd(OAc)(2) to the crude Mixture resulting from the hydroarylation or hydrovinylation step [Pd(OAc)(2), Et(3)N, HCOOH, BU(4)NCI, toluene]. In general, 4-aryl- and 4-vinyl-2,2-dialkyl-3-chromenes are obtained with high regioselectivity and overall yields range from satisfactory to high. Vinyl triflates tend to give higher yields than aryl iodides.
4-Aryl- and 4-Vinyl-2,2-Dialkyl-3-chromenes from Tertiary 3-(o-Bromophenyl)propynols via a Palladium-Catalyzed Hydroarylation/Hydrovinylation–Cyclization Sequenze
ARCADI, Antonio;MARINELLI, Fabio
2006-01-01
Abstract
4-Aryl- and 4-vinyl-2,2-dialkyl-3-chromenes were prepared from tertiary 3-(o-bromoplienyl)propynols and aryl iodides or vinyl triflates through a one-pot process, which involves the addition of t-BuONa, dppf and, where appropriate, fresh Pd(OAc)(2) to the crude Mixture resulting from the hydroarylation or hydrovinylation step [Pd(OAc)(2), Et(3)N, HCOOH, BU(4)NCI, toluene]. In general, 4-aryl- and 4-vinyl-2,2-dialkyl-3-chromenes are obtained with high regioselectivity and overall yields range from satisfactory to high. Vinyl triflates tend to give higher yields than aryl iodides.File in questo prodotto:
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