Addition of Olefins to Aromatic Ketones Catalyzed by Rh(I) Olefin Complexes

Autor:	Maurice Brookhart, Christian P. Lenges
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Olefin fiber Trifluoromethyl Ketone General Chemistry Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Benzophenone Cyclopentene Norbornene Acetophenone
Zdroj:	Journal of the American Chemical Society. 121:6616-6623
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja990702s
Popis:	The rhodium bis-olefin complex [C5Me5Rh(C2H3SiMe3)2], 1, has been shown to be a catalyst for the selective addition of olefins to the ortho position of aromatic ketones. The addition of vinyltrimethylsilane to benzophenone was studied by NMR spectroscopy, which indicated that 1 was the catalyst resting state for this process. This reaction was applied to a series of olefins (allyltrimethylsilane, 1-pentene, norbornene, 2,2‘-dimethyl-3-butene, cyclopentene, and vinyl ethyl ether) and aromatic ketones (benzophenone, 4,4‘-dimethoxybenzophenone, 3,3‘-bis(trifluoromethyl)benzophenone, dibenzosuberone, acetophenone, p-chloroacetophenone, and p-(trifluoromethyl)acetophenone). The dependence of the turnover frequency on substrate concentration was investigated. In the presence of excess ketone the formation of a benzophenone complex, 5, [(C5Me5Rh)2-η4-η4-C6H5C(O)Ph] was observed after consumption of olefin. Active catalyst is regenerated upon addition of olefin to 5. On the basis of kinetic experiments and labeli...
Databáze:	OpenAIRE
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