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. 2013 Sep 9;69(36):10.1016/j.tet.2013.05.050.
doi: 10.1016/j.tet.2013.05.050.

(1-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Eric M Woerly  1 , Jonathan E Miller  1 , Martin D Burke  1
Affiliations

(1-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Eric M Woerly et al. Tetrahedron. .
No abstract available

Keywords: 1,1-disubstituted boronates; 1,1-disubstituted olefins; Iterative cross-coupling; MIDA boronates.

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Figures

Figure 1
Figure 1
1,1-Disubstituted olefins are abundant in pharmaceuticals and natural products.
Figure 2
Figure 2
Proposed mechanism for the formation of 1,1-disubstituted product 3 and 1,2-disubstituted product 4.
Scheme 1
Scheme 1
A 1,1-disubstituted halo boronate building block as a useful reagent for the preparation of 1,1-disubstituted olefins.
Scheme 2
Scheme 2
Synthesis of (1-bromovinyl)-MIDA boronate 2.
Scheme 3
Scheme 3
The unoptimized coupling of building block 2 with phenyl boronic acid provides a mixture of products.
Scheme 4
Scheme 4
MIDA boronate 2 is a substrate for iterative Suzuki-Miyaura coupling reactions.
See this image and copyright information in PMC

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