Direct C-H arylation of electron-deficient heterocycles with arylboronic acids

J Am Chem Soc. 2010 Sep 29;132(38):13194-6. doi: 10.1021/ja1066459.

Abstract

A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

Publication types

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

MeSH terms

  • Boronic Acids / chemistry*
  • Carbon / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Hydrogen / chemistry*

Substances

  • Boronic Acids
  • Heterocyclic Compounds
  • Carbon
  • Hydrogen