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Direct Enamido C(sp2 )-H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to
Hao-Qiang Cao1, Hao-Nan Liu1, Zhe-Yuan Liu1
1Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and, Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin, 300072, P. R. China.
Abstract:
Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2 )-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.
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