Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents

Org Lett. 2013 Apr 5;15(7):1544-7. doi: 10.1021/ol400323z. Epub 2013 Mar 22.

Abstract

By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amines / chemistry*
  • Boranes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Peroxides
  • Phenols / chemistry*

Substances

  • Amines
  • Boranes
  • Ethers
  • Indicators and Reagents
  • Peroxides
  • Phenols
  • di-tert-butyl peroxide
  • Copper