Synthesis of 2,4,5-Trisubstituted Furans via a Triple C(sp(3))-H Functionalization Reaction Using Rongalite as the C1 Unit

Org Lett. 2016 Feb 5;18(3):524-7. doi: 10.1021/acs.orglett.5b03552. Epub 2016 Jan 27.

Abstract

A highly efficient I2/Cu(NO3)2·3H2O-mediated triple C(sp(3))-H functionalization reaction for the synthesis of 2,4,5-trisubstituted furans from aryl methyl ketones and rongalite by employing rongalite as a C1 unit has been developed. This method allows rapid access to (2-acyl-4-methylthio-5-aryl) furans. Preliminary mechanistic studies indicate that in situ generated dimethyl(phenacyl)-sulfonium iodine and HCHO were probably the key intermediates in this transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrocarbons, Iodinated / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Sulfinic Acids / chemistry*

Substances

  • Furans
  • Hydrocarbons, Iodinated
  • Ketones
  • Sulfinic Acids
  • formaldehydesulfoxylate