Organic Chemistry

Metal-Free S-Arylation of Phosphorothioate Diesters and Re-lated Compounds with Diaryliodonium Salts



We developed a direct metal-free S-arylation of phosphorothioate diesters using diaryliodonium salts. The meth-od allows for the preparation under simple conditions of a broad range of S-aryl phosphorothioates, including complex molecules (e.g., dinucleotide- or TADDOL-derivatives), as well as other related organophosphorus compounds arylated at chalcogen. The reaction proceeds with a full retention of the stereogenic center at phos-phorus atom, opening convenient access to P-chiral products. The mechanism of the reaction was established using DFT calculations.


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Supplementary material

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Supporting Information
Experimental procedures, preparation of starting materials, characterization data and copies of NMR spectra for products, computational details and data