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Organoactinide-Mediated Hydrothiolation of Terminal Alkynes with Aliphatic, Aromatic, and Benzylic Thiols. (a), (b) and (c) are commonly used reactions in organic synthesis. Cross-coupling. hydrogenation of olefins. metathesis of olefins. Alkane dehydrogenation.
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Organoactinide-Mediated Hydrothiolation of Terminal Alkynes with Aliphatic, Aromatic, and Benzylic Thiols
(a), (b) and (c) are commonly used reactions in organic synthesis. Cross-coupling hydrogenation of olefins metathesis of olefins Alkane dehydrogenation Catalytic C–C and C–H bond-forming processes Nature 2008, 455, 314–322
first-order: lower alkyne concentrations, zero-order:higher alkyne concentrations
Exchange of deuterium between the thiol and terminal alkyne C-H group is observed with excess alkyne effectively diluting the product deuteration. When the reaction is carried out in a stoichiometric thiol:alkyne ratio, deuterium is equally distributed between the E and Z positions