Arylmagnesium compounds

Scheme 2.4. Preparation of functional arylcoppers from functionalized arylmagnesium compounds.

It is also possible to perform copper-catalyzed alkylation of arylmagnesium compounds. Thus, the copper reagent 48 undergoes a selective cross-coupling [28] with ethyl 4-iodobutyrate to furnish the desired product 49 in 69% yield (Scheme 2.12) [29]. 

Scheme5.43. Reactions of arylmagnesium compounds with nitroarenes [404, 406].

Sapountzis, I. Knochel, P. A new general preparation of polyfunctional diarylamines by the addition of functionalized arylmagnesium compounds to nitroarenes. J. Am. Chem. Soc. 2002, 124, 9390-9391. 

The same group later developed this methodology so that arylmagnesium compounds could be used in the generation of arylzinc complexes for Negishi couplings [160]. 

Gaidis [2] devised two modifications, to distinguish between alkyl- and arylmagnesium compounds ... 

Analogously, 2,3,4,5-tetrahydro-1,2,4-triazines 16 are formed on addition of C-nucleophiles at C-5 when l,2,4-triazin-3-ones and 1,2,4-triazine-3-thiones react with alkyl- or arylmagnesium compounds... 

Treatment of the resulting functionalized arylmagnesium compounds with TiCh affords the corresponding biaryls in good yields (Scheme 3.114). 

EtMgBr-iodoalkane-mediated Coupling of Arylmagnesium Compounds with Tetrahydrofuran via a Radical Process... 

Extremely facile couphng of arylmagnesium compounds and THF by means of an... 

Dohle, W. et al., Pe(III)-catalyzed cross-coupling between functionalized arylmagnesium compounds and alkenyl halides, Synlett, 1901, 2001. 

Bruckner and coworkers reported on the asymmetric halogen/metal exchange to desymme-trize prochiral bis(bromoaryl)alcohols using iPr Mg in the presence of stoichiometric amounts of enantiopure lithium alkoxides or phenoxides. The desymmetrized arylmagnesium compounds were quenched with electrophiles. The best ee/yield combination was (52% ee, 58% yield) (Scheme 28.9) [60]. 

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