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

Authors
  • Sureshkumar, Devarajulu
  • Ganesh, Venkataraman
  • Kumagai, Naoya
  • Shibasaki, Masakatsu
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Nov 24, 2014
Volume
20
Issue
48
Pages
15723–15726
Identifiers
DOI: 10.1002/chem.201404808
PMID: 25252112
Source
Medline
Keywords
License
Unknown

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.

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