Iridium-Catalyzed Formal [4 + 1] Cycloaddition of Biphenylenes with Alkenes Initiated by C-C Bond Cleavage for the Synthesis of 9,9-Disubstituted Fluorenes

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Abstract

An Ir-catalyzed intermolecular reaction of biphenylenes as a C4 unit with various alkenes as a C1 unit gave 9,9-disubstituted fluorenes in moderate to high yields. Preliminary mechanistic studies revealed that this formal [4 + 1] cycloaddition probably proceeds via C-C bond cleavage, alkene insertion, β-hydrogen elimination, intramolecular alkene insertion, and then reductive elimination. An example of enantioselective reaction was also disclosed.

Original languageEnglish
Pages (from-to)1860-1863
Number of pages4
JournalOrganic Letters
Volume18
Issue number8
DOIs
Publication statusPublished - 2016 Apr 15

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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