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Organophosphorus compounds or halophosphines containing halogens of the formula RPX2 and R2PX are grouped under organophosphorus halides. Halophosphines are very significant starting materials and intermediates for the synthesis of various functional groups, such as their corresponding esters, free acids, and amides.
One of the main approaches to synthesizing various substituted phosphines involves the displacement of a halogen atom from the phosphorus compound by an organometallic reagent such as Grignard, lithium species, organozinc, organolead, organomercury, or aluminum-based reagents. Symmetrical and unsymmetrical functionalized aryl phosphines can be synthesized from chlorophosphines and organozinc reagents (Gall, L. et al., Synlett., 2006, 6,954-956). They are useful precursors for the synthesis of many compounds which are useful as plant protection compounds, stabilizers, or catalysts. Substituted diphenylchlorophosphines have increased in importance as they are now employed as metal complexes for asymmetric transformations. Di-tert-butylchlorophosphine and dicyclohexylchlorophosphine are used as ligands in various metal-catalyzed coupling reactions like C-C, C-N, and C-O bond forming reactions. Chlorophosphines react with protected nucleosides to produce phosphoramidites, which are stable for storage and useful in nucleotide coupling reactions. The diastereoisomers of menthylphosphinite boranes are popular synthetic intermediates for enantiopure P-stereogenic compounds. The diastereomeric phosphinites, prepared from alkyldichlorophosphines, are separated and reacted with carbon nucleophiles to give the phosphine-borane with high enantiomeric excess (Review: Wauters, I., et al., Preparation of phosphines through CP bond formation, Beilstein J. Org. Chem. 2014, 10, 10641096).