Journal of the American Chemical Society p. 1351 - 1358 (1989)
Update date:2022-07-30
Topics: Activation of Organocuprates Stabilization of Cuprate Species Control of Regioselectivity Facilitation of Transmetalation Enhancement of Stereochemistry
Lipshutz, Bruce H.
Ellsworth, Edmund L.
Siahaan, Teruna J.
The effects of BF3*Et2O on lower order organocuprate reactions in THF have been investigated so as to determine what factors are responsible for the oftentimes dramatic reaction-rate enhancements observed.From spectroscopic experiments on the reagents alone, supported further by chemical studies, it was found that an orginally formed cuprate (R2CuLi or RR'CuLi) is altered significantly upon exposure to this Lewis acid.The copper-containing species thereby generated, together with BF3, form a more reactive combination and appear to be at least in part responsible forthe accelerated chemistry.
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