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Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes.
- Source :
-
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. - Publication Year :
- 2018
-
Abstract
- 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 <subscript>2</subscript> and (1,3-bis(diphenylphosphino)propane)PdCl <subscript>2</subscript> 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.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 140
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 29420028
- Full Text :
- https://doi.org/10.1021/jacs.7b13601