We report a diaryldiselenide catalyst
for cross-dehydrogenative
nucleophilic functionalization of hydrophosphoryl compounds. The proposed
organocatalytic cycle closely resembles the mechanism of the Atherton–Todd
reaction, with the catalyst serving as a recyclable analogue of the
halogenating agent employed in the named reaction. Phosphorus and
selenium NMR studies reveal the existence of a P –Se bond intermediate,
and structural analyses indicate a stereospecific reaction.
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