Abstract
Phosphines are an important class of ligands in the field of metal-catalysis. This has spurred the development of new routes toward functionalized phosphines. Some of the most important C–P bond formation strategies were reviewed and organized according to the hybridization of carbon in the newly formed C–P bond.
Highlights
Phosphines are an important class of ligands in the field of metal-catalysis
Phosphines are an important class of organophosphorus compounds
They are often used as ligands in metal complex catalysis and they have become a popular reagent for organocatalysis [1]
Summary
Phosphines are an important class of organophosphorus compounds. They are often used as ligands in metal complex catalysis and they have become a popular reagent for organocatalysis [1]. The group of Gaumont has reported their preliminary results for the enantioselective palladium-catalyzed C–P crosscoupling reaction between an achiral vinyl triflate 80c and a racemic secondary phosphine–borane complex 13b (Scheme 23) [165]. When the coupling between aryl iodide 99 and asymmetric secondary phosphine borane 13b was performed in acetonitrile or DMF, the stereochemistry at the phosphorus atom was almost completely retained while the reaction performed in THF or toluene resulted mainly in inversion (Scheme 28) [172,173]. Stelzer and co-workers have developed a general method for the coupling of primary or secondary phosphines instead of their silyl derivatives or borane complexes with functional aryliodides 101 [177,178,179] It should be noted, that the reactions were again limited to (di)phenylphosphine (Scheme 29). The Z-adducts were formed exclusively and isolated as the phosphine sulfides 140 to prevent lower yields by oxidation to the
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