Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes

J Am Chem Soc. 2015 Jan 21;137(2):648-51. doi: 10.1021/ja512115s. Epub 2015 Jan 9.

Abstract

A new radiosynthetic protocol for the preparation of [(11)C]aryl nitriles has been developed. This process is based on the direct reaction of in situ prepared L·Pd(Ar)X complexes (L = biaryl phosphine) with [(11)C]HCN. The strategy is operationally simple, exhibits a remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity compared to previously reported systems. With this procedure, a variety of [(11)C]nitrile-containing pharmaceuticals were prepared with high radiochemical efficiency.

Publication types

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

MeSH terms

  • Carbon Radioisotopes / chemistry
  • Kinetics
  • Nitriles / chemistry*
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Phosphines / chemistry*
  • Temperature*

Substances

  • Carbon Radioisotopes
  • Nitriles
  • Organometallic Compounds
  • Phosphines
  • Palladium
  • phosphine