Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds

Aminoquinoline-directed, palladium-catalyzed sp(3) C-H bond arylation in phosphonamidates and phosphinic amides is reported. The reaction employs Pd(OAc)(2) as a catalyst at 10 mol% loading and cesium phosphate or potassium carbonate as a base in 1,2-dichlorobenzene as a solvent. The directing group can be removed under basic conditions to afford phosphonic acid esters. The chemistry described here is the first example of unactivated sp(3) C-H bond arylation by using a phosphorus-containing directing group.