Palladium-catalyzed coupling of allylic acetates with aryl-and vinylstannanes

L Del Valle, JK Stille, LS Hegedus

Index: Valle, L. Del; Stille, J. K.; Hegedus, L. S. Journal of Organic Chemistry, 1990 , vol. 55, p. 3019 - 3023

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Citation Number: 136

Abstract

A mechanism for the palladium-catalyzed coupling reaction consistent with the experimental data is shown in Scheme I; it is typical of other reactions involving allylic substrates and transmetalation from tin. Thus, oxidative addition of the allyl acetate to palladium (0) produces an v3-allylpalladium acetate. Exchange of acetate for chloride facilitates the transmetalation from tin to palladium, and reductive elimination produces the coupling ...

21040-45-9

(E)-cinnamyl acetate

~85%

~66%

~66%

~51%

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