Ruthenium-Catalyzed Coupling of Aromatic Carbon-Hydrogen Bonds in Aromatic Imidates with Olefins

Catalytic C-H/olcfin coupling can be directed by N, ?ʹ heterocyclic substituents. The Ru(3)(CO)(12)-catalyzed reaction of 4,4-dimethyl-2-(2-methylphenyl)-5,6-dihydro-4H-1,3-oxasine (1) with trieLhoxyvinylsilane gave a mixture of the corresponding 1:1 addition product (3a) and its olefinic analogue (3b) in good yields in ca. a 1:1 ratio. In the case of the reaction of 4,4dimethyl-2-(2-methylphcnyl)-4,5-dihydro-l,3-oxazole (7), the olefinic analogue (8b) of the coupling product (8a) was obtained as the major product. The existence of a new reaction pathway is discussed.