Arylmagnesium bromides

Filler et al. noted that the labile geometric isomer of 7 gives saturated azlactones (18) in 35-40% yields, as well as products of 1,2-addition, when treated with several arylmagnesium bromides. This stereoselectivity appears to be the only reported difference in chemical behavior between isomers of this type. 

Treatment of arylmagnesium bromides with AT -sulfinyldiimidazole yields diaryl sulfoxides [102] [103]... 

Treatment of 112 with an arylmagnesium bromide, followed by dehydration provided access to the substituted alkenes, e.g., 113a and 113b, in moderate yields <06TL6389>. 

A similar electron-transfer mechanism is readily applicable to the reaction between sterically hindered quinones and arylmagnesium bromides, which leads to biaryls as well as quinone anion radical as directly observable species,50 (equation 24). 

Tellurium tetrachloride (as well as tellurium tetrabromide and tellurium tetraiodide) reacts with 4 mol equiv of arylmagnesium bromide, giving rise to diaryl teUurides in high yields. ... 

The preparation of a carboxylic ester by a variant of the Grignard carboxylation route has been described.61 The arylmagnesium bromide is first prepared and added to an excess of diethyl carbonate, conditions which... 

Variable yields of azo compounds were also obtained from reactions of Grignard reagents with diazonium salts, but benzenediazonium tetrafluoroborate gave acceptable yields from arylmagnesium bromides or t-butylmagnesium chloride in THF [19] ... 

ArMgBr —> ArOH. The reagent converts an arylmagnesium bromide or an aryl-lithium into an ate complex (a), which rearranges to b. Phenols are obtained on acid-catalyzed hydrolysis of b. Yields are usually higher from Grignard reagents they are poor with sterically hindered substrates. 

Whereas the treatment of 4-chloroquinazoline with arylmagnesium bromides in tetrahydro-furan results in ring opening (cf. p 149), the Grignard reaction of 4-methoxyquinazoline (9, X = O) and 4-methylsulfanylquinazoline (9, X = S) affords 4-methoxy-2-phcnyl-l,2-dihy-droquinazoline (10, X = O) and 4-methylsulfanyl-2-phenyl-l,2-dihydroquinazoline (10, X = S), respectively. ... 

Sekiya, A., Ishikawa, N. Palladium metal-catalyzed cross-coupling of aryl iodides with arylmagnesium bromides. Synthesis of fluorobiphenyls. J. Organomet. Chem. 1977, 125, 281-290. 

The reaction of l,2-diamino-3-chlorocyclopropenylium ions 21 with arylmagnesium bromides predominantly afforded the coupling products 22. The yields were improved when 1,2-diamino-3-methoxycyclopropenylium ions were used rather than the 3-chloro derivatives. ... 

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