Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)-OH Bonds.

A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)-OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)-OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.