It is known that olefins, especially activated olefins, can be arylated by a conventional two-step Meerwein arylation reaction wherein an arylamine is converted to a diazonium salt, which is then reacted with the olefin in the presence of a copper catalyst, usually cupric chloride.
It is also known that arylated products can be obtained by a one-step Meerwein-type reaction wherein the olefin is treated directly with the arylamine and a nitrite rather than with a diazonium salt. Doyle et al., J. Org. Chem., Vol. 42, 1977, pp. 2431-2436, show that such a one-step Meerwein reaction can be conducted by reacting an arylamine with a large excess of an olefin in an inert polar solvent and in the presence of superstoichiometric amounts of an alkyl nitrite and anhydrous cupric chloride. Kawamatsu et al., Arzneim.-Forsch./Drug Res., Vol. 30(I), No. 5, 1980, pp. 751-758, show that it is possible to conduct such a reaction by reacting an arylamine with an excess of an olefin in an aqueous organic solvent and in the presence of HCl, an inorganic nitrite, and cuprous oxide.
In all of these types of Meerwein reactions, it has been found that the presence of electron-donating groups on the arylamine has generally decreased reactivity and that the product yields obtainable from such arylamines, as well as from other arylamines, could bear improvement.