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Synthesis 2018; 50(09): 1857-1861
DOI: 10.1055/s-0036-1591926
DOI: 10.1055/s-0036-1591926
paper
1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C2 Building Block
This work was supported by Enamine Ltd.Further Information
Publication History
Received: 06 December 2017
Accepted after revision: 12 January 2018
Publication Date:
05 February 2018 (online)
Abstract
1-(Trimethylsilyl)vinyl MIDA boronate — a trifunctional C2 building block — is prepared in only two laboratory steps and 54% overall yield starting from readily available trimethyl(vinyl)silane. The title compound undergoes orthogonal functionalization at either of the groups present in its structure, for example, iodination at the trimethylsilyl moiety, epoxidation at the double bond, and Suzuki–Miyaura coupling at the MIDA boronate.
Key words
organosilicon compounds - organoboron compounds - alkenes - Suzuki–Miyaura coupling - orthogonal reactionsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591926.
- Supporting Information
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