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Reactions of Organomagnesates and Aryl Halides:  Metalation and Nucleophilic Substitution

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journal contribution
posted on 02.02.2004, 00:00 by Julius Farkas, Scott J. Stoudt, Erin M. Hanawalt, Anthony D. Pajerski, Herman G. Richey
Reactions with aryl halides (ArX) of preparations obtained in diethyl ether from an R2Mg compound and a cryptand, an alkali-metal alkoxide, or tetrabutylammonium bromide lead to ArH and ArR. ArH results from magnesium−halogen exchange, and ArR results from aryne formation. Reactions of similar preparations with pyridine lead to formation of larger amounts of substitution product, and those with 2-cyclohexen-1-one to larger amounts of 1,4-addition product, than do reactions of R2Mg alone.