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Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones by Renzo Rossi; Fabio Bellina; Chiara Bechini; Luisa Mannina; Piergiorgio Vergamini is a Chemistry article available to read on EtoBox.

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Absfract : S-Aryl and 5-alkyl substituted @)-3-[l-(aryl)methylidene]-and (E)-3-( I-alkylidene)-3H-furan-2-ones. (E)-9. have been selectively synthesized by cyclization of the corresponding (E)-2-(1-alkynyl)-3aryl/alkylpropenoic acids, (E)-11. in the presence of AgN03 or Pd-catalysts such as rrans-di(pacetato)bis[(di-o-toIylphosphino)benzyl]dipalladiu~n(II) or that constituted of a mixture of Et3N and PdClz(PhCN)z or PdC12(CH3CN)2. in a 3 : 1 molar ratio, respectively. A representative (E)-5-aryl-3-I l-(aryl)methylidene]-3H-furan-2-one, I.P. (E)-Yi, has been also prepared by a tandem process involving a Pd(O)-and Cu(I)-catalyzed cross-coupling reaction between an I-alkyne and a (Z)-3-aryl-2bromopropenoic acid followed by a catalytic intramolecular oxypalladation of the resulting cross-coupled product. However, when this same approach was used IO prepare an (E)-5-akyl-3-[l-(aryI)methyIidene]-3H-furan-2-one, i.e. (E)-9j. a mixture of (E)-9j and the corresponding (E)/(Z)-5-(l-alkylidene)-3-(aryI)methyI-SH-furan-2-one, i.e. (E)/(Z)-20, was obtained. Finally, in an attempt to prepare an (Q-4-alkyI-5-aryI-3-[l-(~I)methylidene]-3H-furaii-2~o~~e, i.e. (E)-14a, by a tandem process involving

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Author

Renzo Rossi; Fabio Bellina; Chiara Bechini; Luisa Mannina; Piergiorgio Vergamini

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1998

Language

EN

Field

Chemistry (Physical Sciences)