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Synfacts 2012; 8(8): 0889
DOI: 10.1055/s-0032-1316629
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Alkylmagnesium Reagents from Boron–Magnesium Exchange

Contributor(s):
Paul Knochel
,
Andreas K. Steib
Reichle MA, Breit B * Albert-Ludwigs-Universität Freiburg, Germany
Preparation of Alkylmagnesium Reagents from Alkenes through Hydroboration and Boron–Magnesium Exchange.

Angew. Chem. Int. Ed. 2012;
51: 5730-5734
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Further Information

Publication History

Publication Date:
19 July 2012 (online)

 
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Key words

boranes - C–C coupling - Grignard reaction

Significance

A novel method for preparing alkylmagnesium reagents has been disclosed. Alkenes undergo a hydroboration with subsequent boron–magnesium exchange to yield the corresponding primary and secondary alkylmagnesium reagents. These organometallic reagents can be used in a wide range of carbon–carbon bond-forming reactions.


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Comment

The key for an efficient boron–magnesium exchange is the use of a pinacolborolane and a 1,4-dimagnesium reagent. The byproducts formed in the course of the exchange reaction did not disturb various subsequent reactions like alkylations, 1,2-additions as well as transition-metal-catalyzed cross-coupling reactions.


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