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Anion-Dependent Switch in C–X Reductive Elimination Diastereoselectivity

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journal contribution
posted on 17.12.2015 by Michael J. Geier, Marzieh Dadkhah Aseman, Michel R. Gagné
Reaction of a complex Pt organometallic species with electrophilic halogen sources in the presence of X ligands changes the mechanism of reductive elimination from a concerted reductive coupling type to an SN2 type reductive elimination. In the absence of the added X ligand the reductive elimination is stereoretentive; in its presence, the process is stereoinvertive. This selectivity hinges on the reactivity of a key five-coordinate Pt­(IV) intermediate with the X ligand.

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