Indium-mediated formation of propargyl ketones from aldehydes or acyl chlorides
✍ Scribed by Jacques Augé; Nadège Lubin-Germain; Latifa Seghrouchni
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 96 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Propargyl ketones were prepared from aldehydes via an indium-mediated alkynylation reaction followed by an indium-mediated Oppenauer oxidation. They were also obtained via an indium-mediated alkynylation of the relevant acyl chlorides.
📜 SIMILAR VOLUMES
Samarium diiodide is an excellent reagent for aldehyde or ketone coupling. With aromatic aldehydes, reactions are very fast with a complete selectivity versus substituents such as cyano, carboxyl or nitro groups.
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Indium-mediated reaction of acyl cyanides 1 with prop-2-ynyl bromides 2 in aqueous media occurs regioselectively to afford either allenic 3 or propargylic ketones 4 depending on the g-substituent of the prop-2-ynyl bromide under the mild conditions.