Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Chem Commun (Camb). 2012 Oct 25;48(83):10319-21. doi: 10.1039/c2cc34340a.

Abstract

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry
  • Amides / chemistry*
  • Boronic Acids / chemistry*
  • Hydrazones / chemistry*
  • Imines / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Zinc / chemistry*

Substances

  • Allyl Compounds
  • Amides
  • Boronic Acids
  • Hydrazones
  • Imines
  • Organometallic Compounds
  • Zinc