Abstract
Hydrophosphination of styrenes has been accomplished with metal salts for the first time. (CuOTf)
2·toluene complex is the catalyst of choice, but CuCl can also be used. “In-situ” EPR and NMR studies suggest Cu(I) as the catalytically active metal species, giving exclusively the
anti-Markovnikov product. Phosphine oxides or
β-ketophosphine oxides can be prepared in one-pot by oxidation with molecular oxygen.
Copper is a selective catalyst for the
anti-Markovnikov hydrophosphination of styrenes.
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► Hydrophosphination of styrenes is catalyzed by copper salts. ► Tertiary phosphines by Anti-markovnikov addition are exclusively formed. ► Lewis acid and radical pathways contribute to the mechanism of addition. ► Silver and manganese salts are also catalysts for the hydrophosphination.