Gold(III)- versus gold(I)-induced cyclization: synthesis of six-membered mesoionic carbene and acyclic (aryl)(heteroaryl) carbene complexes

Angew Chem Int Ed Engl. 2013 Jan 7;52(2):758-61. doi: 10.1002/anie.201207961. Epub 2012 Nov 21.

Abstract

The golden state: selective 5-exo- and 6-endo-cyclizations of an alkynyl benzothioamide have been achieved. The selectivity is controlled by the oxidation state of the gold precursor (+I or +III), yielding two new types of carbene ligand: an (aryl)(heteroaryl)carbene and a six-membered mesoionic carbene. Mes=2,4,6-trimethylphenyl.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis
  • Methane / chemistry
  • Stereoisomerism

Substances

  • carbene
  • Gold
  • Methane