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.

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Access to P-chiral H-phosphinates via desymmetrization of hypophosphite esters was investigated. The use of chiral auxiliaries, chiral catalysts, and of a bulky prochiral group that could lead to kinetic resolution was explored. A chiral NMR assay for enantiomeric excess determination of H-phosphinates was developed. An asymmetric route to C-chiral H-phosphinates is also examined and an assay was developed.

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Palladium-Catalyzed Cross-Coupling of H-Phosphinate Esters with Chloroarenes. -A wide range of aromatic and heteroaromatic phosphinates is prepared. -(DEAL, E. L.; PETIT, C.; MONTCHAMP*, J.-L.; Org. Lett. 13 (2011) 12, 3270-3273, http://dx.doi.org/10.1021/ol201222n ; Dep. Chem., Tex. Christian Univ., Fort Worth, TX 76129, USA; Eng.) -R. Steudel