Organometallic reagents and cross-coupling
11 real reactions from the literature: Grignard formation on aryl chlorides, primary alkyl bromides and aryl bromides; acetylide formation on terminal alkynes; Grignard protonolysis on Grignard reagents; and more. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.
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Grignard formation: chlorobenzene (an aryl chloride) with 1) Mg, iPrOH; 2) HCl, H2O gives benzene (the Grignard reagent).
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Acetylide formation: propyne (a terminal alkyne) with NaNH2; NH3 (l) gives the metal acetylide.
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Grignard protonolysis: a Grignard reagent with H2SO4; H2O gives pentane (the alkane).
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Ullmann coupling: 1-chloro-4-nitrobenzene (an aryl chloride) and phenol with KOH, Δ; Cu (cat.) gives 1-nitro-4-phenoxybenzene (the diaryl ether).
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Wurtz coupling: bromobenzene (an aryl bromide) with Na; CH3CH2OCH2CH3 gives butylbenzene (the coupled product).
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Grignard formation: 2-bromomesitylene (an aryl bromide) with Mg; CH3CH2OCH2CH3 gives the Grignard reagent.
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Grignard formation: 1-bromo-2-methylpropane (a primary alkyl bromide) with Mg; CH3CH2OCH2CH3 gives the Grignard reagent.
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Grignard formation: butyl bromide (a primary alkyl bromide) with Mg; CH3CH2OCH2CH3 gives the Grignard reagent.
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Grignard formation: 1-bromonaphthalene (a naphthyl bromide) with Mg; CH3CH2OCH2CH3 gives the Grignard reagent.
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Grignard formation: 1-bromo-3-chlorobenzene (an aryl chloride) with Mg; CH3CH2OCH2CH3, Δ gives the Grignard reagent.
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Grignard formation: methyl chloride and a Grignard reagent with CH3CH2OCH2CH3; Mg gives the Grignard reagent.