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Arylation of Unsaturated Compounds by Diazonium Salts (The Meerwein Arylation Reaction)

  1. Christian S. Rondestvedt Jr.

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or024.03

Organic Reactions

Organic Reactions

How to Cite

Rondestvedt, C. S. 2011. Arylation of Unsaturated Compounds by Diazonium Salts (The Meerwein Arylation Reaction). Organic Reactions. 24:3:225–259.

Author Information

  1. E. I. du Pont de Nemours and Company, Inc.,, Jackson Laboratory, Wilmington, Delaware

  1. I am greatly indebted to Carolyn Sidor, du Pont Experimental Station, for invaluable assistance in the later stages of the literature survey.

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The arylation of unsaturated compounds by diazonium salts with copper salt catalysis was first disclosed by Meerwein. Meerwein arylation proceeds best when the double bond is activated by an electron attracting groups such as carbonyl, cyano, aryl, vinyl, ethynyl or chloro. The net result is the union of the aryl group with the carbon atom beta to the activating group, either by substitution of a beta-hydrogen atom of by addition of Ar and Cl to the double bond. The generally accepted mechanism of the reaction involves the aryl radical from the diazonium salt, though the manner of its formation and subsequent reaction is still controversial

Keywords:

  • arylation;
  • unsaturated compounds;
  • Meerwein arylation reaction;
  • diazonium salts;
  • unsaturated components;
  • side reactions;
  • synthetic applications;
  • experimental conditions