Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent

Org Lett. 2001 Aug 23;3(17):2729-32. doi: 10.1021/ol016333y.

Abstract

[reaction: see text]. A simple, palladium-catalyzed method to convert aryl halides to the parent anilines using lithium bis(trimethylsilyl)amide (LiN(SiMe3)2) is reported. The reaction is catalyzed by Pd(dba)2 and P(t-Bu)3 and can be run with as little as 0.2 mol % of catalyst. The reaction is faster than competing generation of benzyne intermediates and, therefore, provides the aniline products regiospecifically.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Ammonia / chemistry*
  • Halogens / chemistry*
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Trimethylsilyl Compounds

Substances

  • Amines
  • Halogens
  • Organometallic Compounds
  • Trimethylsilyl Compounds
  • lithium bis(trimethylsilyl)amide
  • Palladium
  • Ammonia