Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

George Iakobson, Junyi Du, Alexandra Martha Zoya Slawin, Petr Beier*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

Original languageEnglish
Pages (from-to)1494-1502
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume11
DOIs
Publication statusPublished - 26 Aug 2015

Keywords

  • Borylation
  • Diazonium salts
  • Iodination
  • Pyridine
  • Sulfur pentafluorides

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