Abstract
X = Cl, Br; n = 1-3 4-(Difluoroiodo)toluene-induced domino λ3-iodanation-1,4-halogen shift-ring enlargement-fluorination reaction of 5-halopentynes with a four-, five-, or six-membered carbocycle afforded the ring-expanded (E)-δ-fluoro-β-halovinyl- λ3-iodanes stereoselectively in high yields, probably via the intermediacy of five-membered halonium ions. Use of internal alkynes makes it possible to synthesize tetrasubstltuted β-halovinyl-λ3- iodanes with defined stereochemistry.
| Original language | English |
|---|---|
| Pages (from-to) | 3335-3338 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 9 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 16 Aug 2007 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Cite this
Ochiai, M., Hirobe, M., Yoshimura, A., Nishi, Y., Miyamot, K., & Shiro, M. (2007). Internal delivery of soft chlorine and bromine atoms: Stereoselective synthesis of (E)-β-halogenovinyl(aryl)-λ3-iodanes through domino λ3-lodanation-1,4-halogen shift-fluorination of alkynes. Organic Letters, 9(17), 3335-3338. https://doi.org/10.1021/ol071345q