Iron-Catalyzed ortho-Selective C-H Borylation of 2-Phenylpyridines and Their Analogs

Yusuke Yoshigoe, Yoichiro Kuninobu

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Treatment of 2-phenylpyridines (or their analogs) with a 9-bicycloboranonane dimer (9-BBN dimer) in the presence of a catalytic amount of a commercially available iron salt, FeBr3, gave ortho-borylated products in moderate to excellent yields with good functional group tolerance. The reaction proceeded in good yield, even in gram-scale, and also occurred at the C-H bond of heteroaromatic compounds. The cost of the C-H borylation is dramatically lower than that of a previously reported similar palladium-catalyzed reaction. The products exhibit an intramolecular B-N Lewis acid-base interaction and fluoresce in both solution and solid states due to their electron push-pull structures.

Original languageEnglish
Pages (from-to)3450-3453
Number of pages4
JournalOrganic letters
Volume19
Issue number13
DOIs
Publication statusPublished - Jul 7 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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