63263-75-2Relevant academic research and scientific papers
Efficient synthesis of mono- and diarylphosphinic acids: a microwave-assisted palladium-catalyzed cross-coupling of aryl halides with phosphinate
Kalek, Marcin,Stawinski, Jacek
experimental part, p. 10406 - 10412 (2010/02/27)
A general, efficient method for the microwave-assisted synthesis of mono- and diarylphosphinic acids from anilinium phosphinate and aryl halides, using Pd(0) and Xantphos as a supporting ligand, was developed.
Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds
Montchamp, Jean-Luc
, p. 2388 - 2406 (2007/10/03)
This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.
Palladium-catalyzed cross-coupling reaction of anilinium hypophosphite with alkenyl bromides and triflates: Application to the synthesis of GABA analogs
Dumond, Yves R,Montchamp, Jean-Luc
, p. 252 - 260 (2007/10/03)
Alkenyl bromides and triflates undergo palladium-catalyzed cross-coupling with anilinium hypophosphite to afford mono-substituted phosphinates (salts of alkenylphosphonous acids). The reaction is an extension of our previously reported methodology for the synthesis of aryl- and benzyl-phosphonous acids. Our preliminary results show that the best reaction conditions are observed with Pd(OAc)2/dppp as a catalyst, in refluxing benzene or tetrahydrofuran. This novel P-C bond forming reaction conditions are observed synthesis of (1,2,3,6-tetrahydropyridin-4-y1)-methylphosphinic acid (TPMPA), a selective competitive antagonist for GABAc receptors. The divergent synthesis proceeds through protected (1,2,3,6-tetrahydropyridin-4-y1)-phosphinic acid, a previously unknown isoguvacine-like GABA analog. This synthetic intermediate is also an ideal precursor to other biologically interesting GABA analogs.
