- Phosphorus-carbon bond formation: Palladium-catalyzed cross-coupling of H-phosphinates and other P(O)H-containing compounds
-
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
- Berger, Olivier,Petit, Christelle,Deal, Eric L.,Montchamp, Jean-Luc
-
supporting information
p. 1361 - 1373
(2013/06/26)
-
- Hydrophosphinylation of unactivated terminal alkenes catalyzed by nickel chloride
-
The room-temperature hydrophosphinylation of unactivated monosubstituted alkenes using phosphinates (ROP(O)H2) and catalytic NiCl2 in the presence of dppe is described. The method is competitive with prior palladium-catalyzed reactio
- Ortial, Stephanie,Fisher, Henry C.,Montchamp, Jean-Luc
-
p. 6599 - 6608
(2013/07/26)
-
- Palladium-catalyzed cross-coupling of H-phosphinate esters with chloroarenes
-
The palladium-catalyzed cross-coupling reaction between H-phosphinate esters and chloroarenes or chloroheteroarenes is described. This reaction is the first general metal-catalyzed phosphorus-carbon bond-forming reaction between a phosphorus nucleophile and chloroarenes.
- Deal, Eric L.,Petit, Christelle,Montchamp, Jean-Luc
-
supporting information; experimental part
p. 3270 - 3273
(2011/08/03)
-
- Alkylation of H-phosphinate esters under basic conditions
-
(Chemical Equation Presented) An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.
- Abrunhosa-Thomas, Isabelle,Sellers, Claire E.,Montchamp, Jean-Luc
-
p. 2851 - 2856
(2008/02/01)
-