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

By Janine Cossy, 100

The Grignard response is without doubt one of the primary organometallic reactions, frequently utilized in alcohol syntheses. With transition metals like iron, cobalt and nickel or with noble metals like copper, silver and palladium, glossy Grignard reagents might be designed in reactivity, selectivity and practical crew tolerance. This booklet, written through overseas specialists, offers an summary on well timed Grignard chemistry concerning transition metals.

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78: Cross-coupling of vinylmagnesium halides and secondary alkyl halides [84]. Takanami et al. have used the palladium-catalyzed coupling of silyl-bearing alkylmagnesium reagents with bromide-functionalized porphyrins to enable access to a variety of motifs (Fig. 79) [92]. The silyl group could be further elaborated by e. g. oxidation or reaction with electrophiles (including DAST, to yield a fluoride group). Fig. 79: Functionalization of porphyrin compounds [92]. 1With Aryl Electrophiles Hayashi et al.

Successfully arylated an example of a vinyl chloride compounds using a TADDOL-derived ligand 12 [40]; only one example was presented, alongside a series of other reactions catalyzed by the same palladium/ligand system (Fig. 54). Fig. 54: Cross-coupling of 1-chlorocyclopentene enabled by TADDOL-derived ligand 12 [40]. Skrydstrup and co-workers have arylated various vinyl phosphate compounds using two different arylmagnesium halide compounds [77]. The catalyst employed was simply PdCl2, used in THF at room temperature.

90: Cross-coupling of chloro-dienes and chloro-enynes with arylmagnesium chlorides [75]. Aoyama et al. have used an axially chiral P,N-ligand 41 in palladium-catalyzed cross-couplings of 1-phenylethylmagnesium chloride with β-bromostyrenes [98, 99]. The configuration at the alkene was retained in each case, while the ee of the products varied from 71–80 %. The S configuration was obtained from each reaction. Some examples of the products prepared can be found in Fig. 91. Fig. 91: Enantioselective Grignard cross-coupling [98].

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