Carbon-phosphorus cross-coupling

Scheme 6.67 Palladium-catalyzed carbon-phosphorus cross-coupling.

CARBON-PHOSPHORUS BOND-FORMING CROSS-COUPLINGS 386... 

Utility of Enol and Aryl Triflates. Enol and aryl triflates are extensively used for cross-coupling reactions, the formation of carbon-carbon, carbon-tin, carbon-nitrogen, carbon-sulfur, carbon-phosphorus, and carbon-halogen bonds, and reduction/ deoxygenation. In recent examples, they were used to form enamines or enamides or were eliminated to cyclooctynes for copper-free cycloadditions in biological systems. 

The development of a palladium-catalyzed cross-coupling process for the preparation of vinylphosphonates by Hirao was one of the turning points for the preparation of vinylphos-phonates [368]. His chemistry was operationally simple and utilized a readily available palladium(O) compound as the catalyst and triethylamine as the base. The temperatures required for his reaction were mild compared to Arbuzov chemistry, and the phosphorus-carbon bond-forming reaction was compatible with a wide range of functional groups. 

Schwan AL. Palladium catalyzed cross-coupling reactions for phosphorus-carbon bond formation. Chem. Soc. Rev. 2004 33 218-224. 

---