Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp²)-H/alkene functionalization

Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11338-41. doi: 10.1002/anie.201407175. Epub 2014 Sep 4.

Abstract

This study describes a new rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp(2))-H bond and addition/protonolysis of an alkene C=C bond. This method is applicable to a wide range of 5-aryl-2,3-dihydro-1H-pyrroles and internal alkynes, and results in the assembly of the spiro[indene-1,2'-pyrrolidine] architectures in good yields with excellent regioselectivities.

Keywords: alkynes; annulation; heterocycles; rhodium; spiro compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkynes / chemistry*
  • Catalysis
  • Indenes / chemistry
  • Pyrroles / chemistry*
  • Pyrrolidines / chemistry
  • Rhodium / chemistry*
  • Spiro Compounds / chemistry

Substances

  • Alkenes
  • Alkynes
  • Indenes
  • Pyrroles
  • Pyrrolidines
  • Spiro Compounds
  • indene
  • Rhodium