Reaction of organic compounds with new stable heterocuprates containing 8-quinoloxy and 2-pyridyloxy ligands

Abstract

It has been found that two new heterocuprates containing 8-quinoloxy and 2-pyridyloxy ligands exhibit improved thermal stability and also have a good reactivity in typical organocuprate reactions. The cuprates are easily prepared by the addition of alkyllithium to 8-quinoloxy or 2-pyridyloxy copper and are stable after standing at 0℃ for 30 min. The cuprates are effectively utilized for the synthesis of ketones from acid chlorides and utilization of alkyl group is also of synthetic significance. Reaction of cuprates with α,β-unsaturated conjugated ketones proceeds rapidly and cleanly in most cases. However, in the case of β-disubstituted conjugated ketones, the use of boron trifluoride etherate as an additive in an equimolar ratio improves the yields whereas the reactions in the absence of boron trifluoride etherate give the low yields due to steric hindrance of the reactants. Furthermore, these heterocuprates can be used in substitution reaction of alkyl halides and epoxides.