Copper‐Catalyzed Cross‐Coupling Reaction of α‐Halo‐N‐Tosylhydrazones with H‐Phosphoryl Compounds to Afford Alkenylphosphoryl Compounds

The copper‐catalyzed reaction of α‐halo‐N‐tosylhydrazones with H‐phosphoryl compounds is reported to afford alkenylphosphoryl compounds in modest to good yields. The reaction may take place via a copper‐promoted Bamford‐Stevens‐type reaction of an α‐phosphorylated diazo intermediate. The diazo intermediate is trapped by an excess H‐phosphoryl compound to give α, N‐bisphosphoryl hydrazone in the absence of a copper catalyst. C−P bond formation. The copper‐catalyzed coupling reaction of α‐halo‐N‐tosylhydrazones with H‐phosphoryl compounds is reported to selectively afford alkenylphosphoryl compounds. The reaction with excess H‐phosphoryl compounds gave α, N‐bisphosphoryl hydrazones without a copper catalyst.