Synthesis of fluoranthenes and indenocorannulenes: Elucidation of chiral stereoisomers on the basis of static molecular bowls

Yao Ting Wu, Tomoharu Hayama, Kim K. Baldridge, Anthony Linden, Jay S. Siegel

Research output: Contribution to journalArticlepeer-review

96 Citations (Scopus)

Abstract

Cycloaromatization of a peri diyne with an external alkyne provides a general route to indenofused polynuclear aromatics. Fluoranthenes 9 (or 13) are easily accessible in good to excellent yields (75-99%; 18 examples) from the reaction of symmetric (or asymmetric) diynes 4 and alkynes 5 (or norbornadiene) in the presence of Wilkinson's catalyst. This formal [(2+2)+2] cycloaddition can also be applied to generate various indenocorannulenes 28 from 2,3-diethynylcorannulene derivatives 27 and alkynes 5. The indenocorannulenes 28 exist in a static bowl form at room temperature with bowl-to-bowl inversion barriers higher than 24 kcal/mol. This barrier renders the rate of inversion slow enough at room temperature to establish a class of chiral, bowl-shaped stereoiomers containing no tetrahedrally ligated atoms. The crystal structure of 28g provides insight into the bowl-shaped geometry of these compounds. This new synthetic method occurs under neutral conditions and tolerates various functional groups (e.g., alkyl, aryl, alcohols, and esters).

Original languageEnglish
Pages (from-to)6870-6884
Number of pages15
JournalJournal of the American Chemical Society
Volume128
Issue number21
DOIs
Publication statusPublished - 2006 May 31

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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