The highly regioselective aerobic oxidative cyclization of aromatic, heteroaromatic and alkenyl acids with alkynes in the presence of catalytic amounts of [{RuCl(2)(p-cymene)}(2)], AgSbF(6) and Cu(OAc)(2)·H(2)O providing isocoumarin derivatives was investigated.
Aromatic and heteroaromatic ketoximes underwent cyclization with alkynes in the presence of a catalytic amount of [{RuCl(2)(p-cymene)}(2)] and NaOAc to give isoquinoline derivatives in good to excellent yields in a highly regioselective manner.
The reactions of substituted acetophenones with diphenylacetylene in the presence of [{RuCl 2 (p-cymene)} 2 ] (2 mol-%), AgSbF 6 (8 mol-%), and Cu(OAc) 2 ·H 2 O (25 mol-%) in 1,2-dichloroethane at 120°C for 10 h provided substituted indenol derivatives in good-to-excellent yields. Under similar reaction conditions, unsymmetrical alkynes such as 1-phenyl-1-propyne, 1-phenyl-1-butyne, 1-phenyl-2-(trimethylsilyl)-acetylene, and a substituted enyne also reacted efficiently with substituted acetophenones to afford the corresponding indenol derivatives in a highly regioselective manner. The
A highly regioselective ruthenium-catalyzed ortho-arylation of substituted N-alkyl benzamides with aromatic boronic acids in the presence of [{RuCl(2)(p-cymene)}(2)], AgSbF(6), and Ag(2)O is described. Further, ortho-arylated N-alkyl benzamides were converted into fluorenones in the presence of trifluoroacetic anhydride and HCl.
The highly regioselective ortho-arylation of acetanilides with aromatic boronic acids in the presence of a Ru(II) complex (3 mol%), AgSbF6 (12 mol%), Cu(OTf)2 (20 mol%) and Ag2O (1.0 eq.) is described. Later, ortho-arylated acetanilides were converted into phenanthridine and carbazole derivatives by using Ph3PO and Tf2O or palladium or Cu(OTf)2 catalysts.
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