Practical thiol surrogates and protective groups for arylthiols for Suzuki-Miyaura conditions

J Org Chem. 2006 Mar 3;71(5):2203-6. doi: 10.1021/jo052624z.

Abstract

We have developed practical thiol surrogates and arylthiol protective groups for the Suzuki-Miyaura reaction. 2-Ethylhexyl-3-mercaptopropionate and 4-(2'-mercaptoethyl)pyridine were shown to be not only good thiol surrogates but also good protective groups for thiol. We have demonstrated toleration of these protective groups under aqueous Suzuki-Miyaura conditions.

MeSH terms

  • 3-Mercaptopropionic Acid / analogs & derivatives*
  • 3-Mercaptopropionic Acid / chemical synthesis
  • 3-Mercaptopropionic Acid / chemistry
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Sulfhydryl Compounds / chemical synthesis
  • Sulfhydryl Compounds / chemistry*

Substances

  • 2-ethylhexyl-3-mercaptopropionic acid
  • 4-(2'-mercaptoethyl)pyridine
  • Pyridines
  • Sulfhydryl Compounds
  • 3-Mercaptopropionic Acid