115049-29-1Relevant articles and documents
Phosphorus-carbon bond formation: Palladium-catalyzed cross-coupling of H-phosphinates and other P(O)H-containing compounds
Berger, Olivier,Petit, Christelle,Deal, Eric L.,Montchamp, Jean-Luc
supporting information, p. 1361 - 1373 (2013/06/26)
Two generally applicable systems have been developed for the cross-coupling of P(O)H compounds with Csp2-X and related partners. Palladium catalysis using a ligand/additive combination, typically either xantphos/ethylene glycol or 1,1-bis(diphenylphosphino)ferrocene/1,2- dimethoxyethane, with diisopropylethylamine as the base, proved to be generally useful for the synthesis of numerous P-C containing compounds. Routinely, 2 mol% of catalyst are employed (less than half the amount typically employed in most other literature reports). In most cases, excellent results are obtained with a variety of electrophiles (RX, where R=alkenyl, allyl, alkynyl, etc.). The full account of our studies is disclosed, including tandem hydrophosphinylation/ coupling and coupling/coupling for doubly catalytic phosphorus-carbon bond formation. The methodology compares favorably with any existing literature report. The use of an additive appears to be a generally useful strategy to control the reactivity of phosphinylidene compounds. Copyright
Direct monoalkylation of alkyl phosphinates to access H-phosphinic acid esters
Abrunhosa-Thomas, Isabelle,Ribiere, Patrice,Adcock, Alicia C.,Montchamp, Jean-Luc
, p. 325 - 331 (2007/10/03)
Simple alkyl phosphinates prepared by the silicate esterification method can be alkylated under Barbier-like conditions with butyl lithium at -78 °C followed by warming to room temperature. The method is limited to the more reactive electrophile such as allylic bromides and alkyl iodides. With these electrophiles good yields of H-phosphinic acid esters are generally obtained in a straightforward manner. Georg Thieme Verlag Stuttgart.
