ChemCatChem
ChemCatChem
4 years ago

Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel

Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel
Juventino J. García, Rosa E. Islas
The use of simple and inexpensive NiCl2⋅6 H2O as a catalyst precursor for C−P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. Control experiments showed the in situ formation of (RO)2P(O)H as the species that undergo the addition into the C≡C bond at the alkynes to yield the product of P−H addition. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand. This method is useful for the preparation of organophosphonates for both phenylacetylene as a terminal alkyne model and internal alkynes in yields that range from good to modest. Back to the hydrophosphonylation: The use of inexpensive NiCl2⋅6 H2O as a catalyst precursor for C−P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. (RO)2P(O)H formed in situ undergoes addition to the alkyne C≡C bond. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand.

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

DOI: 10.1002/cctc.201700974

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