A new inexpensive copper-catalyzed denitrogenative CÀP coupling reaction of pyridotriazoles with P(O)H compounds has been developed. The reaction proceeds via a process of coppercatalyzed P(O)ÀH insertion into the pyridyl carbene intermediates generated in situ from pyridotriazoles. This reaction provides a new and effective method for the synthesis of a variety of 2picolylphosphoryl compounds.
A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.
A novel CuI-catalyzed cross-coupling of propargyl epoxides with P(O)H compounds is disclosed. The reaction proceeded efficiently under mild conditions to give 4-phosphoryl 2,3-allenols in good to high yields with excellent selectivity. The utility of the products was demonstrated and a plausible mechanism was also proposed.
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.
A tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)PF6]‐catalyzed dehydrative reaction of 1‐(2‐hydroxyphenyl)propargyl alcohols with diarylphosphine oxides has been developed to provide an efficient synthesis of phosphorylated benzofurans in good to high yields. In the presence of a catalytic amount of an organic base, a variety of H‐phosphonates and H‐phosphinates can also be employed as good substrates to produce the corresponding products in moderate yields. The reaction has significant economical and ecological advantages since the formation of a new C(sp3)–P bond and the benzofuran framework could both be achieved using an inexpensive copper catalyst with water produced as the sole by‐product. Some synthetic transformations of the product have also been demonstrated.magnified image
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