Phosphorylation of C(sp<sup>3</sup>)–H Bonds via 1,4-Palladium Migration
Xiaoming Ji, Yanzhen Chen, Jian‐Guo Fu, Shu‐Sheng Zhang, Chen‐Guo Feng
Abstract
1,4-Palladium migration has emerged as a reliable method for directed C–H functionalization. In contrast to coupling with carbon nucleophiles, limited examples with heteroatom nucleophiles have been reported. Herein we report a palladium-catalyzed intermolecular C(sp3)–H phosphorylation reaction via 1,4-palladium migration, which is often difficult because of the strong coordination of phosphorus reagents to palladium catalysts. Phosphorylation of C(sp3)–H bonds is accomplished in good reaction yields with excellent regioselectivity. The judicious selection of the phosphine ligand proved to be the key to the success of this cascade process.
Topics & Concepts
PalladiumChemistryNucleophilePhosphineRegioselectivityCombinatorial chemistryReagentCatalysisLigand (biochemistry)Organic chemistryBiochemistryReceptorCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOrganophosphorus compounds synthesis