4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: An Efficient and Selective 2-Carbon Building Block for Vinylboronate Suzuki-Miyaura Coupling Reactions

Andrew P. Lightfoot; Steven J. R. Twiddle; Andrew Whiting

doi:10.1055/s-2005-862354

LETTER

4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: An Efficient and Selective 2-Carbon Building Block for Vinylboronate Suzuki-Miyaura Coupling Reactions

Andrew P. Lightfoot^a, Steven J. R. Twiddle^b, Andrew Whiting*^b
^a GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK
^b Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK
Fax: +44(191)3843747; e-Mail: andy.whiting@durham.ac.uk;

Abstract

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Abstract

An extremely simple and efficient palladium-catalyzed coupling procedure for the synthesis of functionalized styrenes and dienes is utilized to demonstrate how 4,4,6-trimethyl-2-vinyl-1,3,2-dioxaborinane can be employed to selectively undergo Suzuki-Miyaura coupling with a range of halide substrates.

Key words

Suzuki-Miyaura coupling - palladium(0) - vinylboronate ester - chemoselectivity

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References

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Typical Procedure, Conditions A.
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