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Triphenylphosphine is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides. The anionic phosphine is usually isolated as the trisodium salt, which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions. It is also used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyse C-C coupling reactions in organic synthesis.
Finds widespread use as a complexing agent with transition metals, either in the preparation of stable complexes, or as an additive in metal-promoted reactions. See also Tri(o-tolyl)phosphine, A12093 and Tri(2-furyl)phosphine, L13329.
Azides can be converted selectively to amines, in the presence of ester, epoxide or nitro groups, by reduction to iminophosphoranes (Staudinger reaction), followed by hydrolysis. For reviews, see: Tetrahedron, 37, 437 (1981); 48, 1353 (1992):
In suitable circumstances, the iminophosphorane may undergo intramolecular aza-Wittig reaction: Tetrahedron, 45, 6375 (1989):
Reviews: Aza-Wittig reaction in heterocyclic synthesis: Org. Prep. Proced. Int., 24, 209 (1992); Iminophosphoranes as building blocks for the preparation of N-containing heterocycles: Synthesis, 1197 (1994).
For use in peptide and other coupling reactions, see 2,2'-Dipyridyl disulfide, A11118.
For use in the Mitsunobu reaction for conversion of alcohols to alkylating agents, see N-Guanylurea sulfate, A19106, and Diisopropyl azodicarboxylate, L10386. See also 1,2-Bis(diphenylphosphino)ethane, A11419.
Loghmani, M. H.; Shojaei, A. F. Reduction of cobalt ion improved by lanthanum and zirconium as a triphenylphosphine stabilized nano catalyst for hydrolysis of sodium borohydride. Int. J. Hydrogen Energy 2015, 40 (20), 6573-6581.
Nirmala, M.; Prakash, G.; Viswanathamurthi, P.; Malecki, J. G. An attractive route to transamidation catalysis: Facile synthesis of new o-aryloxide-N-heterocyclic carbene ruthenium (II) complexes containing trans triphenylphosphine donors. J. Mol. Catal. A: Chem. 2015, 403, 15-26.
Hazard Statements: H302-H317-H373
Harmful if swallowed. May cause an allergic skin reaction. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P280g-P301+P312a-P363-P321-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves. IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Wash contaminated clothing before reuse. Specific treatment (see label). Dispose of contents/container in accordance with local/regional/national/international regulations.