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Catalytic Synthesis of Triaryl Phosphates from White Phosphorus
Author(s) -
Armstrong Kenneth M.,
Kilian Petr
Publication year - 2011
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201100046
Subject(s) - chemistry , catalysis , phosphate , white phosphorus , phenol , phenols , phosphorus , chlorine , organic chemistry , inorganic chemistry , iron phosphate , tris , medicinal chemistry , nuclear chemistry , biochemistry
Triaryl phosphates were synthesized from white phosphorus and phenols under aerobic conditions and in the presence of iron catalysts and iodine. Full conversion to phosphates was achieved without the use of chlorine, and the reactions do not produce acid waste. Triphenyl phosphate, tritolyl phosphate and tris(2,4‐di‐ tert ‐butyl)phenyl phosphate were synthesized by this method with high selectivities. Various iron(III) diketonates were used to catalyze the conversion. Mechanistic studies showed that the reaction proceeds by formation of PI 3 , then O=PI(OPh) 2 before the final formation of the phosphate. The nucleophilic substitution of O=PI(OPh) 2 with phenol to form O=P(OPh) 3 was found to be the rate‐limiting step.