Rhodium(III)-catalyzed C2-selective carbenoid functionalization and subsequent C7-alkenylation of indoles

Chem Commun (Camb). 2014 Jun 21;50(49):6483-6. doi: 10.1039/c4cc01593b. Epub 2014 May 12.

Abstract

Here a new, mild and versatile method for efficient synthesis of a diverse range of 2-acetate substituted indoles via Rh(III)-catalyzed and alcohol-mediated C2-selective carbenoid insertion functionalization of indoles by α-diazotized Meldrum's acid has been developed. Furthermore, for the first time, a Rh(III)/Cu(II)-catalyzed direct C7-alkenylation of such functionalized products has also been demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Copper / chemistry
  • Dioxanes / chemistry
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Rhodium / chemistry*

Substances

  • Alkenes
  • Dioxanes
  • Indoles
  • Copper
  • Meldrum's acid
  • Rhodium