Tetrahedron p. 10103 - 10114 (1992)
Update date:2022-07-27
Topics:
Monteiro, Nuno
Gore, Jacques
Balme, Genevieve
In the presence of a palladium(0) complex and potassium t-butoxide, the acetylenic compounds 2 bearing in δ a nucleophilic functionality are smoothly transformed with excellent yields, either into 2,2-difunctionalized methylene cyclopentanes or into monofunctionalized 2-methylcyclopentenes. Each of these compounds can be specifically obtained depending on the choice of the experimental conditions. A set of diverse reactions involving mainly potassium hydride as the base showed clearly that HPdOtBu is not the active catalytic species which is mainly a σ-ethynylpalladium hydride formed by the metal insertion in the acetylenic carbon hydrogen bond.
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Doi:10.1021/acs.orglett.0c03723
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