Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides

Org Lett. 2013 Apr 5;15(7):1536-9. doi: 10.1021/ol400320q. Epub 2013 Mar 14.

Abstract

A robust and efficient protocol for the introduction of the dioxolanylethyl moiety onto various aryl and heteroaryl halides has been developed, providing cross-coupling yields up to 93%. Copper-catalyzed borylation of 2-(2-bromoethyl)-1,3-dioxolane with bis(pinacolato)diboron followed by treatment with potassium bifluoride provides the key organotrifluoroborate reagent.

Publication types

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

MeSH terms

  • Borates / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry
  • Dioxolanes / chemical synthesis*
  • Dioxolanes / chemistry
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry
  • Molecular Structure
  • Potassium / chemistry*

Substances

  • Borates
  • Dioxolanes
  • Hydrocarbons, Chlorinated
  • Copper
  • Potassium