Arylphosphinic acids synthesis

G. Keglevich, A. Szekrenyi, M. Sipos, K. Ludanyi, 1. Greiner, Synthesis of cyclic aminomethylphosphonates and aminomethyl-arylphosphinic acids by an efficient microwave-mediated phospha-Mannich approach. Heteroatom Chem. 19 (2008) 207-210. 

With this last point in mind, the synthesis of mono-, bis- and tra-sulfonated triphenylphosphine will be described, but the same methodology can be applied to the preparation of other sulfonated arylphosphines. In general, these phosphines are made by direct sulfonation using fuming sulfuric acid (oleum) [21], The extent of sulfonation is determined by the SO3 strength, as well as factors such as the temperature and time of the reaction. The monosulfonated phosphine (tppms) is prepared using oleum of 20% SO3 strength, with typically 30% SO3 used... 

Interest in the Staudinger reaction of phosphines with azides, and the Mit-sunobu reaction involving nucleophilic attack by phosphorus at nitrogen in esters of diazodicarboxylic acids, has continued. Systems of the type (205) have been obtained from the reactions of secondary arylphosphines with azides. Treatment of these with butyllithium results in deprotonation to form the diaminophosphonium diazaylides (206). Phosphazenes have been prepared from azido-quinolines and -triazines, and also from diazoketones " and polycyanocyclopropanes. The Staudinger reaction has been employed in the synthesis of phosphorus-containing dendrimers, and in new approaches to amide and peptide synthesis. The reaction has also been used in a high-... 

A general and efficient method for the microwave-assisted synthesis of mono- and diarylphosphinic acids (579) and (581) from anihnium 7f-phosphinate (580) and aryl halides, using Pd(0) and Xantphos as a supporting ligand, has been developed by Stawihski and Kalek (Scheme A2)P The procedure was highly efficient and provided a rapid access to a broad spectrum of arylphosphinate derivatives. 

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