A syn outer-sphere oxidative addition: the reaction mechanism in Pd/Senphos-catalyzed carboboration of 1,3-enynes - Université de Pau et des Pays de l'Adour Access content directly
Journal Articles Chemical Science Year : 2023

A syn outer-sphere oxidative addition: the reaction mechanism in Pd/Senphos-catalyzed carboboration of 1,3-enynes

Ziyong Wang
Walid Lamine
Shih-Yuan Liu
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Abstract

We report a combined experimental and computational study of Pd/Senphos-catalyzed carboboration of 1,3enynes utilizing DFT calculations, 31 P NMR study, kinetic study, Hammett analysis and Arrhenius/Eyring analysis. Our mechanistic study provides evidence against the conventional inner-sphere b-migratory insertion mechanism. Instead, a syn outer-sphere oxidative addition mechanism featuring a Pd-p-allyl intermediate followed by coordination-assisted rearrangements is consistent with all the experimental observations.
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Dates and versions

hal-04007526 , version 1 (28-02-2023)

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Ziyong Wang, Walid Lamine, Karinne Miqueu, Shih-Yuan Liu. A syn outer-sphere oxidative addition: the reaction mechanism in Pd/Senphos-catalyzed carboboration of 1,3-enynes. Chemical Science, 2023, 14 (8), pp.2082 - 2090. ⟨10.1039/d2sc05828f⟩. ⟨hal-04007526⟩
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