| Autor: |
Olivares AM; University of Rochester , Rochester, New York 14627-0216, United States., Weix DJ; University of Rochester , Rochester, New York 14627-0216, United States.; University of Wisconsin-Madison , Madison, Wisconsin 53706, United States. |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of the American Chemical Society [J Am Chem Soc] 2018 Feb 21; Vol. 140 (7), pp. 2446-2449. Date of Electronic Publication: 2018 Feb 08. |
| DOI: |
10.1021/jacs.7b13601 |
| Abstrakt: |
The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5'-bis(trifluoromethyl)-2,2'-bipyridine)NiBr 2 and (1,3-bis(diphenylphosphino)propane)PdCl 2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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