The tin(IV) compound, Cp*2SnCl2, was shown to successfully add Ph2PH across a range of alkene substrates. It was found that the catalytic dehydrocoupling of Ph2PH was a competitive reaction, but reactions run under one atmospher of H2 increased both the selectivity and relative rate of reaction toward hydrophosphination. Typical consumption of Ph2PH for these reactions were 79–100%, with the formation of hydrophoshination products between 68–86% and the formation of Ph4P2, the product of dehydocoupling, between 2–7%. The reactivity of the tin(IV) compound, Ph2SnCl2, and the tin(II) compound, Cp*2Sn, were also probed. Compared to Cp*2SnCl2, Ph2SnCl2 showed limited catalytic reactivity; however, the product distribution was more selective toward hydrophosphination, with almost no conversion to Ph4P2. It was found that Cp*2Sn was not a catalyst for these hydrophosphination reactions. Alkene substrate scope and mechanistic analysis will be presented.

Tin catalyzed hydrophosphination of secondary phosphines

251st National Meeting (2016)

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