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Synthesis of Single Geometric Oxime Ether by Palladium Catalyzed Suzuki Cross Coupling Reaction

Library 3B

Conventionally, diaryl oxime ethers [Ar(C=NOR )Ar’] are prepared by a condensation reaction between a benzophenone and an alkoxyamine. These diaryl oxime ethers are known to be geometrically stable and do not readily undergo E/Z isomerization. Unfortunately, the condensation reaction leads to a mixture of E/Z isomers that are very difficult to separate. Pd-catalyzed coupling reactions involving alkenyl halides generally result in retained geometry. In contrast, few examples have been reported of metal-catalyzed cross coupling reactions with imidoyl halides [RC (X)=NR’] and their resulting geometry. Of these, very few involve the coupling of an imidoyl halide containing a heteroatom attached to the nitrogen atom. This work discusses the investigation of Suzuki cross coupling reactions of N-alkoxybenzimidoyl halides[ArC(X)=NOR ] and boronic acids or trifluoroborate salts to synthesize single geometric isomers of diaryl oxime ethers.