Lithium dihydropyridine dehydrogenation catalysis: a group 1 approach to cyclisation of diamine-boranes

Ross McLellan, Alan R. Kennedy, Samantha A. Orr, Stuart D. Robertson, Robert E. Mulvey

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17 Citations (Scopus)
88 Downloads (Pure)

Abstract

In reactions restricted previously to a ruthenium catalyst, a 1-lithium-2-alkyl-1,2-dihydropyridine complex is shown to be a competitive alternative dehydrogenation catalyst for the transformation of diamine boranes to cyclic 1,3,2-diazaborolidines, which can in turn be smoothly arylated in good yields. This study establishes the conditions and solvent dependence of the catalysis via NMR monitoring, with mechanistic insight provided by NMR (including DOSY) experiments and X-ray crystallographic studies of several model lithio intermediates.
Original languageEnglish
Pages (from-to)1036-1041
Number of pages6
JournalAngewandte Chemie International Edition
Volume56
Issue number4
Early online date21 Dec 2016
DOIs
Publication statusPublished - 19 Jan 2017

Keywords

  • NMR monitoring
  • X-ray crystallography
  • lithio intermediates
  • catalytic processes
  • solvent dependence
  • catalysts
  • dehydrogenation
  • catalysis
  • dihydropyridine
  • diaminoboranes
  • lithium

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