sp3 C-H bond arylation directed by amidine protecting group: alpha-arylation of pyrrolidines and piperidines

J Am Chem Soc. 2006 Nov 8;128(44):14220-1. doi: 10.1021/ja064481j.

Abstract

A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.

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

  • Amidines / chemistry*
  • Carbon / chemistry*
  • Hydrocarbons, Aromatic / chemistry*
  • Hydrogen / chemistry*
  • Molecular Structure
  • Piperidines / chemistry*
  • Pyrrolidines / chemistry*
  • Stereoisomerism

Substances

  • Amidines
  • Hydrocarbons, Aromatic
  • Piperidines
  • Pyrrolidines
  • Carbon
  • Hydrogen