Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts

J Org Chem. 2005 Apr 1;70(7):2696-700. doi: 10.1021/jo047758b.

Abstract

[reaction: see text] The CuI/L-proline sodium salt catalyzed coupling reaction of aryl halides with sulfinic acid salts readily occurs at 80-95 degrees C in DMSO to give the corresponding aryl sulfones in good to excellent yields. This process is well-tolerated by a wide range of functional groups including hydroxyl, amino, acetanilide, ketone, ester, and nitrile. Using this method, 4-phenylsulfonyl- and 4-methanesulfonyl-substituted L-phenylalanine derivatives are prepared.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Halogens / chemistry*
  • Iodides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Proline / chemistry*
  • Salts
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfinic Acids / chemistry*
  • Sulfones / chemical synthesis*

Substances

  • Halogens
  • Iodides
  • Salts
  • Sulfinic Acids
  • Sulfones
  • Copper
  • cuprous iodide
  • Proline