Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative

Ilijana Kikaš, O. Horváth, Irena Škorić

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A simple and efficient protocol is utilized for the synthesis of novel functionalized benzobicyclo[3.2.1]octadiene derivatives by photocatalytic oxygenation of a furan derivative using an anionic free-base porphyrin as well as cationic and anionic manganese(III) porphyrins under different reaction conditions. The course and yields of these reactions were compared to those of the thermal reaction using m-chloroperbenzoic acid as the oxidizing agent. The deviating reaction pathways with anionic and cationic metalloporphyrins may be attributed to simultaneous electronic and steric effects. Application of free-base and metalated water-soluble porphyrins for photocatalytic oxygenation of the furan ring fused to the rigid methano-bridged skeleton proved to be regioselective and flexible compared to the thermal reactions with mCPBA, giving at the same time novel potentially biologically active bicyclo[3.2.1]octenes with the basic skeleton of which is incorporated in many natural compounds.

Original languageEnglish
Pages (from-to)6255-6259
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number47
DOIs
Publication statusPublished - Nov 23 2011

Fingerprint

Oxygenation
Porphyrins
Skeleton
Hot Temperature
Metalloporphyrins
Derivatives
Oxidants
Water
furan
3-chloroperbenzoic acid
manganese(III) porphyrin

Keywords

  • Benzobicyclo[3.2.1]octadienes
  • Furan derivative
  • Photocatalytic oxygenation
  • Porphyrins

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative. / Kikaš, Ilijana; Horváth, O.; Škorić, Irena.

In: Tetrahedron Letters, Vol. 52, No. 47, 23.11.2011, p. 6255-6259.

Research output: Contribution to journalArticle

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