Organic Letters
Organic Letters
5 years ago

Silver-Free Direct Synthesis of Alkynylphosphine Oxides via spC–H/P(O)–H Dehydrogenative Coupling Catalyzed by Palladium

Silver-Free Direct Synthesis of Alkynylphosphine Oxides via spC–H/P(O)–H Dehydrogenative Coupling Catalyzed by Palladium
Tieqiao Chen, Jian-Qiu Zhang, Li-Biao Han, Ji-Shu Zhang
A silver-free palladium-catalyzed dehydrogenative phosphorylation of terminal alkynes with hydrogen phosphine oxides has been developed. Both aromatic and aliphatic terminal alkynes including those bearing functional groups coupled readily with hydrogen phosphine oxides, producing the corresponding value-added alkynylphosphine oxides in good to excellent yields. This reaction could be easily conducted at gram scales (10 mmol) without any decrease of the reaction efficiency, showing highly potential synthetic value in organic synthesis. A plausible Pd(0)/Pd(II) mechanism is proposed.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02389

DOI: 10.1021/acs.orglett.7b02389

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