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Creators/Authors contains: "Lamine, Walid"

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  1. ; ; ; ; ; ; (, Journal of the American Chemical Society)
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  2. ; ; ; (, Chemical Science)
    We report a combined experimental and computational study of Pd/Senphos-catalyzed carboboration of 1,3-enynes 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 β-migratory insertion mechanism. Instead, a syn outer-sphere oxidative addition mechanism featuring a Pd-π-allyl intermediate followed by coordination-assisted rearrangements is consistent with all the experimental observations. 
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  3. ; ; ; ; ; (, Organic & Biomolecular Chemistry)
    The first aromatic Claisen rearrangement of a 1,2-azaborine is described along with a quantitative kinetic comparison of the reaction of the azaborine with its direct all-carbon analogue. The azaborine A rearranged in a clean, regioselective fashion and reacted faster than the all-carbon substrate B at all temperatures from 140–180 °C. Activation free energies were extracted from observed first-order rate constants (A: Δ G ‡298K = 32.7 kcal mol −1 ; B: Δ G ‡298K = 34.8 kcal mol −1 ) corresponding to a twenty fold faster rate for A at observed reaction temperatures. DFT calculations show that the rearrangement proceeds via a concerted six-membered transition state and that the electronic structure of the BN and CC rings is mostly responsible for the observed regioselectivity and relative reactivity. 
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  4. ; ; ; ; ; ; ; (, The Journal of Organic Chemistry)
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