Grignard Reagents and Transition Metal Catalysts. by Janine Cossy, 100

By Janine Cossy, 100

The Grignard response is likely one of the primary organometallic reactions, usually utilized in alcohol syntheses. With transition metals like iron, cobalt and nickel or with noble metals like copper, silver and palladium, sleek Grignard reagents will be designed in reactivity, selectivity and practical team tolerance. This ebook, written via overseas specialists, offers an summary on well timed Grignard chemistry related to transition metals.

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74 above) [37]. The use of a more electron-donating ligand bearing two dialkylphosphine sites was often necessary to achieve this reaction. Fig. 83: Cross-coupling of aryl tosylates with alkylmagnesium halides (isolated yields) [37]. Using the [PdCl(μ-Cl)(37)]2 catalyst system described previously, Ackermann et al. demonstrated the cross-coupling of alkylmagnesium chlorides and bromides with a selection of aryl halides (Fig. 84) [86]. Notably, this same catalyst system is active for the reaction between arylmagnesium halides and alkyl halides.

Reactions were catalyzed by [Ni(acac)2] (acac = acetoacetonate). Fig. 2: Cross-coupling reactions catalyzed by [Ni(acac)2], disclosed by Corriu et al. [8]. In the same year, Kumada et al. published the use of [NiCl2(dppe)] (dppe = 1,2-bis(diphenylphosphino)ethane) for the cross-coupling of alkyl and arylmagnesium bromide reagents with aryl and vinyl chloride species (Fig. 3) [9]. The catalyst in this case bore a bidentate phosphine ligand; dppe outperformed 1,3-bis(diphenylphosphino) propane (dppp) and 1,2-bis(dimethylphosphino)ethane (dmpe), which in turn outperformed complexes bearing two PPh3, PEt3 or PPh2Me ligands.

87: Catalyst structure influences the rates of competing processes [96]. Bull et al. have developed a method for the cross-coupling of aziridinylmagnesium chloride compounds with aryl bromides (Fig. 88) [97]; the former were generated by sulfonyl-magnesium exchange. 5 equiv ZnCl2, it is most likely that the corresponding zinc species undergoes transmetalation, rather than the organomagnesium halide. Fig. 88: Arylation of aziridines [97]. ’s [PdCl2(dppf)]-catalyzed method was also used to couple sec-butylmagnesium chloride with two model vinyl electrophiles, with very good to excellent yield (Fig.

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Grignard Reagents and Transition Metal Catalysts. by Janine Cossy, 100
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