Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group

Xiao Yang Chen, Seyma Ozturk, Erik J. Sorensen

Research output: Contribution to journalArticle

61 Scopus citations

Abstract

The first synthesis of substituted fluorenones directly from benzaldehydes and aryl iodides via a Pd(II)-catalyzed C(sp2)-H functionalization cascade is reported. Featuring anthranilic acid as an inexpensive transient directing group, the process is compatible with a variety of benzaldehydes and aryl iodides. A three-step synthesis of the antiviral drug Tilorone was completed in an excellent overall yield (40%), demonstrating the utility of this method.

Original languageEnglish (US)
Pages (from-to)1140-1143
Number of pages4
JournalOrganic Letters
Volume19
Issue number5
DOIs
StatePublished - Mar 3 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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