Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles

Molecules. 2017 Jul 14;22(7):1178. doi: 10.3390/molecules22071178.

Abstract

A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity.

Keywords: metal-free; regiodivergent; α,β-unsaturated electrophiles.

MeSH terms

  • Aldehydes / chemistry*
  • Carbon / chemistry*
  • Chemistry Techniques, Synthetic / methods*
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Metals / chemistry*
  • Molecular Structure
  • Nitrobenzenes / chemistry*
  • Salts / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Metals
  • Nitrobenzenes
  • Salts
  • 4-nitrobenzyl chloride
  • Carbon