Studies on samarium diiodide initiated addition reaction of fluoroalkyl iodides to alkynes and its mechanism
✍ Scribed by Shengming Ma; Xiyan Lu
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 423 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Abetract: Samarium diiodide was found to be an effective initiator in the addition reaction of fluoroalkyl iodides to alkynes. A single electrontransfer radical chain mechanism was proposed for the reaction based on ESR studies and other experimental results.
Samarium diiodide, a strong single-electron dpnor, has shown its versatile synthetic utility in organic chemistry. In all the reactions reported so far, samarium diiodide has been used in excess amount as a reductant, while its catalytic property in radical reaction has not been disclosed. Recently, we reported the first example of uging samarium diiodide as a catalyst to promote the radical addition reaction, in which samarium diiodide was found to be able to initiate the addition reaction of fluoroalkyl iodides to olefins under very mild condition with high chemical reactivity and regioslectivity in fairly good yield. In this paper, we wish to report the addition reaction of fluoroalkyl iodides to alkynes.