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Synfacts 2020; 16(08): 0946
DOI: 10.1055/s-0040-1706902
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

The Grignard Reaction

Contributor(s):
Paul Knochel
,
Juri Skotnitzki
Grignard V. University of Lyon, France
Some New Organometallic Combinations of Magnesium and their Application to the Synthesis of Alcohols and Hydrocarbons.

C. R. Acad. Sci 1900;
130: 1322-1324
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Further Information

Publication History

Publication Date:
21 July 2020 (online)

 
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Key words

Grignard reagents - aldehydes - ketones - alcohols

Significance

In 1900, V. Grignard reported the reaction of an alkyl halide with magnesium metal in diethyl ether leading to a cloudy solution of an organometallic compound (RMgX). Subsequent reaction with aldehydes or ketones, later named the Grignard reaction, afforded the corresponding ­alcohols. Grignard reagents have become an indispensable part of today’s organic synthesis and they are widely used for carbon–carbon bond formations. As acknowledgement of this great discovery, V. Grignard was awarded with the Nobel prize in 1912.


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Comment

The formation of the Grignard reagent proceeds most likely through a single-electron transfer (SET) mechanism and takes places on the metal surface. The mechanism of the addition of the Grignard reagent to the carbonyl group is not fully understood. However, it is thought that the reaction takes places via a radical (stepwise) or a concerted pathway forming the corresponding alkoxides.


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Reviews

E. C. Ashby Q. Rev. Chem. Soc., 1967, 21, 259-285; J. F. Garst, M. P. Soriaga Coord. Chem. Rev. 2004, 248, 623-652.


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