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DOI: 10.1055/s-0033-1339616
Zinc-Mediated Regiodiverse Synthesis of Vinyl Bromide Derivatives and Their in situ Palladium-Catalysed Cross-Coupling Reactions
Publication History
Received: 02 July 2013
Accepted after revision: 11 July 2013
Publication Date:
15 August 2013 (online)
Dedicated to Prof. Dr. Reinhard W. Hoffmann on the occasion of his 80th birthday. Many thanks for the fruitful and entertaining discussions.
Abstract
The synthesis of vinyl bromide derivatives was realised by a zinc-mediated addition of a benzylic bromide to a terminal alkyne. The geometry of the C=C bond is dependent on the amount of zinc powder applied. When 5 mol% of Zn is used, the Z-configured vinyl bromide is generated while with 150 mol% the E-geometry is obtained predominantly. In a three-component one-pot reaction, the in situ generated vinyl bromides were reacted further in a palladium-catalysed Suzuki cross-coupling reaction utilizing aromatic boronic acids to obtain trisubstituted double bonds in good overall yields. The reactions were conducted on a 5–20 mmol scale to visualise that the reactions are also capable of generating larger amounts of products.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For key references, see:
For the synthesis of alkenyl halides, see: