Alkoxide-Promoted Selective Hydroboration of N-Heteroarenes: Pivotal Roles of in situ Generated BH 3 in the Dearomatization Process

Eunchan Jeong, Joon Heo, Sehoon Park*, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

While numerous organo(metallic)catalyst systems were documented for dearomative hydroboration of N-aromatics, alkoxide base catalysts have not been disclosed thus far. Described herein is the first example of alkoxide-catalyzed hydroboration of N-heteroaromatics including pyridines, providing a broad range of reduced N-heterocycles with high efficiency and selectivity. Mechanistic studies revealed an unprecedented counterintuitive dearomatization pathway, in which 1) pyridine-BH 3 adducts undergo a hydride attack by alkoxyborohydrides, 2) in situ generated BH 3 serves as a catalytic promoter, and 3) 1,4-dihydropyridyl borohydride is in a predominant resting state.

Original languageEnglish
Pages (from-to)6320-6325
Number of pages6
JournalChemistry - A European Journal
Volume25
Issue number25
DOIs
StatePublished - 2 May 2019
Externally publishedYes

Keywords

  • N-heteroarenes
  • alkali base catalyst
  • dearomatization
  • hydroboration
  • ionic mechanism

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