160343-11-3

Upstream product

• 591-50-4 iodobenzene 
• 133471-17-7 (R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 108-86-1 bromobenzene 

Downstream Products

• 160400-84-0 (R)-5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl thymidin-5'-yl phenylphosphonate 
• 1370586-79-0 C₅₆H₆₆N₆O₁₄P₂ 

Relevant academic research and scientific papers

Preparation of arylphosphonates by palladium(O)-catalyzed cross-coupling in the presence of acetate additives: Synthetic and mechanistic studies

An efficient protocol for the synthesis of arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.

Microwave-assisted palladium-catalyzed cross-coupling of aryl and vinyl halides with H-phosphonate diesters

(Chemical Equation Presented) A general and efficient method for the microwave-assisted formation of the C-P bond was developed. Using a prevalent palladium catalyst, Pd(PPh3)4, a quantitative cross-coupling of various H-phosphonate diesters with aryl and vinyl halides was achieved in less than 10 min. The reactions occurred with retention of configuration at the phosphorus center and in the vinyl moiety. Using this protocol, several C-phosphonates, including those bearing nucleoside and cholesteryl moieties, were prepared in high yields.