Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

Md Shafiqur Rahman, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of triphenylene-fused phosphole oxides has been achieved through two distinct C–H functionalization reactions as key steps. The phosphole ring was constructed by a three-component coupling of 3-(methoxymethoxy)phenylzinc chloride, an alkyne, and dichlorophenylphosphine, involving the regioselective C–H activation of the C2 position of the arylzinc intermediate via 1,4-cobalt migration. The resulting 7-hydroxybenzo[b]phosphole derivative was used for further π-extension through Suzuki–Miyaura couplings and a Scholl reaction, the latter closing the triphenylene ring. The absorption and emission spectra of the thus-synthesized compounds illustrated their nature as hybrids of triphenylene and benzo[b]phosphole.

Original languageEnglish
Pages (from-to)524-529
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
Publication statusPublished - 2020 Mar 27
Externally publishedYes

Keywords

  • C–H functionalization
  • Fluorescence
  • Phosphole
  • Polycyclic aromatic hydrocarbons
  • Triphenylene

ASJC Scopus subject areas

  • Organic Chemistry

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