Regioselective reductive hydration of alkynes to form branched or linear alcohols

J Am Chem Soc. 2012 Oct 24;134(42):17376-9. doi: 10.1021/ja307145e. Epub 2012 Oct 16.

Abstract

The regioselective reductive hydration of terminal alkynes using two complementary dual catalytic systems is described. Branched or linear alcohols are obtained in 75-96% yield with ≥25:1 regioselectivity from the same starting materials. The method is compatible with terminal, di-, and trisubstituted alkenes. This reductive hydration constitutes a strategic surrogate to alkene oxyfunctionalization and may be of utility in multistep settings.

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Alkynes / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alcohols
  • Alkynes