Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles

J Am Chem Soc. 2006 Sep 20;128(37):12050-1. doi: 10.1021/ja063278l.

Abstract

An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne-vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne-vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.

Publication types

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

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Cyclization
  • Germanium / chemistry*
  • Gold / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Isomerism
  • Organometallic Compounds / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Silicon / chemistry*
  • Tin / chemistry*

Substances

  • Alkynes
  • Heterocyclic Compounds
  • Organometallic Compounds
  • Pyrroles
  • Germanium
  • Tin
  • Gold
  • Silicon