C-N bond cleavage of allylic amines via hydrogen bond activation with alcohol solvents in Pd-catalyzed allylic alkylation of carbonyl compounds

J Am Chem Soc. 2011 Dec 7;133(48):19354-7. doi: 10.1021/ja209373k. Epub 2011 Nov 9.

Abstract

Hydrogen-bond-activated C-N bond cleavage of allylic amines was realized in Pd-catalyzed allylic alkylation to form the C-C bond product. The method could be expanded to a series of allylic amines and carbonyl compounds with excellent results. It provides a new and convenient access to C-C bond formation based on Pd-catalyzed allylic alkylation of allylic amines by using only inexpensive alcohol solvents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkylation
  • Allyl Compounds / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Hydrogen Bonding
  • Palladium / chemistry*

Substances

  • Alcohols
  • Allyl Compounds
  • Amines
  • Palladium