Arylation

In contrast to alkylation , which means the introduction of alkyl groups , arylation describes the introduction of an aryl group into a chemical , usually organic compound . The arylation is not limited to the linkage between an aryl radical and a carbon atom, but is also used for the linkage with heteroatoms such as nitrogen , oxygen , sulfur or phosphorus . A special case of arylation is the introduction of a phenyl radical , which is referred to as phenylation .

Many arylation reactions can be achieved through metal-catalyzed reactions . For example, transition metal- catalyzed reactions such as the Suzuki , Stille , Kumada or Sonogashira coupling , the Heck , Meerwein or Ullmann reaction , and the Stephens-Castro or Negishi coupling are suitable for this purpose .

Copper- catalyzed arylation of a phenyl halide to biphenyl (Ullmann coupling).

The arylation of electron-poor heteroaromatics such as pyridine or quinoline can also be carried out by nucleophilic ipso- substitution with organometallic compounds such as organolithium or Grignard compounds .

Individual evidence

1. ↑ ^{a b} entry on arylation. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
2. ↑ JA Joules, K. Mills: Heterocyclic Chemistry , 5th Edition, pp. 125-141, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 .