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Grignard Reaction

Grignard reaction   Named Reactions in Organic Synthesis

Reaction category:
Reactions involving carbonyl compounds

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In 1900, French chemist Victor Grignard discovered that when treating an alkyl halide with magnesium metal in diethyl ether, a cloudy solution of an organomagnesium compound was formed. This substance would subsequently react with aldehydes and ketones to produce secondary and tertiary alcohols respectively.

These organomagnesium compounds became known as Grignard reagents and their addition across carbon–heteroatom multiple bonds is now called the Grignard reaction. Very shortly after this discovery, the Grignard reaction became one of the best known and most versatile carbon– carbon bond forming reactions.

Grignard reagents are typically prepared by reacting alkyl, aryl or vinyl halides with magnesium metal in aprotic nucleophilic solvents such as ethers. The carbon magnesium bond is highly polar, making Grignard reagents excellent carbon nucleophiles. As a result, the subsequent carbon–carbon bond-forming step is straightforward.

Grignard reagents have been used in the synthesis of several natural products, including the total synthesis of (±)-lepadiformine and several natural and modified cyclotetrapeptide trapoxins.

Mechanism of the Grignard reaction

Grignard reaction mechanism


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Pericyclic and photochemical reactions NEW!

Radical reactions

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle formation

Transition metal-catalyzed couplings

Oxidation

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Electrophilic addition reactions


Some relevant Alfa Aesar products for the Grignard reaction:

Magnesium, turnings, 99+%
Magnesium turnings, 99.8% (metals basis)
Magnesium turnings, 1cm (0.4in) & down, Puratronic®, 99.98% (metals basis)
Magnesium turnings, 99.8% (metals basis)
Magnesium powder, -20+100 mesh, 99.8% (metals basis)
Allylmagnesium chloride, 1M in MeTHF
Isopropylmagnesium chloride - LiCl complex, 1M in MeTHF
Phenylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSeal? bottles
Methylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSeal? bottles
Benzylmagnesium chloride, 1M in MeTHF
Methylmagnesium bromide, 3M in ether
Phenylmagnesium bromide, 3M in 2-MeTHF
Benzylmagnesium chloride, 1-2M in THF
Ethylmagnesium bromide, 3M in ether
Phenylmagnesium bromide, 3M in ether


We have many Grignard reagents within the Alfa Aesar portfolio.

 

 

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