Electrophilic borylation of terminal alkenes with BBr3/2,6-disubstituted pyridines

Shinya Tanaka, Yuki Saito, Takaya Yamamoto, Tetsutaro Hattori

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A variety of terminal alkenes, as well as heteroaromatic compounds, are borylated by the combined use of BBr3/2,6-dichloropyridine (B3) or BBr3/2,6-lutidine (B5). α,α-Diarylalkenes prefer the former reagent combination, while other alkenes prefer the latter. Mechanistic considerations strongly suggest that the former and latter reactions proceed through electrophilic substitution reactions with BBr3 and [BBr2·B5]+BBr4-, respectively.

Original languageEnglish
Pages (from-to)1828-1831
Number of pages4
JournalOrganic letters
Volume20
Issue number7
DOIs
Publication statusPublished - 2018 Apr 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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