Direct catalytic addition of alkylnitriles to aldehydes by transition-metal/NHC complexes

Devarajulu Sureshkumar, Venkataraman Ganesh, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

Direct catalytic addition of alkylnitriles to aldehydes allows for an atom-economical access to β-hydroxynitriles under proton transfer conditions. Direct use of alkylnitriles as pronucleophiles has been hampered due to their low acidity resulting in an inability to generate α-cyano carbanions in a catalytic manner. A transition metal/N-heterocyclic carbene (NHC) complex prepared from [{Rh(OMe)(cod)}2] and an imidazolium-based carbene was identified as an effective catalyst to promote the reaction with as little as 1.25 mol% of catalyst loading. The corresponding Rh complex, derived from chiral triazolium salt, rendered the reaction enantioselective, albeit with moderate enantioselectivity.

Original languageEnglish
Pages (from-to)15723-15726
Number of pages4
JournalChemistry (Weinheim an der Bergstrasse, Germany)
Volume20
Issue number48
DOIs
Publication statusPublished - 2014 Nov 24
Externally publishedYes

Keywords

  • alkylnitriles
  • asymmetric catalysis
  • cooperative catalysis
  • N-heterocyclic carbenes
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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