NaOAc-Assisted Aerobic Oxidation Protocol for the Synthesis of Pentacoordinate Chalcogenyl Spirophosphoranes with P–Se/P–S Bonds under Open Air

The NaOAc-assisted aerobic oxidation reaction of pentacoordinate
hydrospirophosphoranes and dichalcogenyl compounds with open air as
a green oxidant has been developed under mild conditions. A series
of novel pentacoordinate spirophosphoranes with P–Se/P–S
bonds were synthesized in excellent yields. The reaction mechanism
was determined by 31P nuclear magnetic resonance tracing
experiments, high-resolution mass spectrometry tracing experiments,
and X-ray diffraction analysis. The method features a broad substrate
scope, good functional group tolerance, and a high degree of atomic
utilization and is meaningful for the synthesis of bioactive chalcogenphosphate
compounds with chalcogen and phosphorus moieties.