Early-Transition-Metal-Mediated Activation and Transformation of White Phosphorus
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Author(s)
Cossairt, Brandi M.
Piro, Nicholas A.
Cummins, Christopher C.
Date Issued
February 2010
Journal
Chemical Reviews
Publisher
American Chemical Society
Citation
Cossairt, Brandi M., Nicholas A. Piro, and Christopher C. Cummins. “Early-Transition-Metal-Mediated Activation and Transformation of White Phosphorus.” Chemical Reviews 110.7 (2010) : 4164-4177.
Version
Author's final manuscript
Abstract
Phosphorus-containing molecules are ubiquitous in the world around us and the synthetic and industrial
utilization of phosphorus has prospered for over a century. The industrial reduction of
phosphate rock (apatite, Ca[subscript 10](PO[subscript 4])[subscript 6](X)[subscript 2], X = OH, F, Cl, or Br) to white phosphorus, P[subscript 4], exceeds
500,000 tons annually as P[subscript 4] still represents the major commercial P-atom source for the
production of organophosphorus compounds utilized by the food, detergent, specialty chemical,
and pharmaceutical industries. The present day synthesis of organophosphorus compounds is a
multi-step process in which P[subscript 4] is first chlorinated to generate PCl[subscript 3], which in turn is functionalized
by reaction with an appropriate Grignard or organolithium reagent, or by treatment with a halogenated
organic compound and a powerful reducing agent. For example, the industrial method
for triphenylphosphine preparation is based on the high temperature reaction of chlorobenzene
with phosphorus trichloride in the presence of molten sodium. From both a safety and a sustainability
standpoint, the need for PCl[subscript 3] as an intermediate for the production of organophosphorus
compounds is unpalatable and methods that circumvent its use are of great interest. This has provoked
intensive investigations into the mild and controlled activation of P[subscript 4], a clear objective being
the development of catalytic methods for phosphorus incorporation into organic molecules.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/cr9003709
