3 years ago

Silver-Catalyzed Atom-Economic Hydrophosphorylation of Propargyl Epoxides: An Access to 4-Phosphoryl 2,3-Allenols and Stereodefined 1-Phosphoryl 1,3-Dienes

Silver-Catalyzed Atom-Economic Hydrophosphorylation of Propargyl Epoxides: An Access to 4-Phosphoryl 2,3-Allenols and Stereodefined 1-Phosphoryl 1,3-Dienes
Ming Zhang, Li-Biao Han, Jianlin Yang, Ruwei Shen
The highly regioselective nucleophilic ring opening of propargyl epoxides by P(O)H compounds based on a silver catalyst is reported. A variety of P(O)H compounds including H-phosphonates, H-phosphinates and diarylphosphine oxides can be used to produce 4-phosphoryl 2,3-allenols under mild conditions. The stereoselective synthesis of 1-phosphoryl 1,3-butadienes from 4-phosphoryl 2,3-allenols and organoboronic acids via a palladium-catalyzed coupling reaction is also described.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700421

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