Direct Enamido C(sp2)-H Diphosphorylation Enabled by PCET-triggered Double Radical Relay: Access to gem-Bisphosphonates

Chemistry : a European Journal
Hao-Qiang CaoJun-An Ma

Abstract

Here 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(sp 2 )-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a same 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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