Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals

J Am Chem Soc. 2017 Jan 11;139(1):115-118. doi: 10.1021/jacs.6b12712. Epub 2016 Dec 23.

Abstract

Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl- as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or directing groups. This one-pot transformation allows unprecedented functional group tolerance and it is well-suited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper(I) salt is required.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Copper / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*

Substances

  • Amines
  • Organometallic Compounds
  • Copper