Metal-Free <i>S</i> -Arylation of Phosphorothioate Diesters and Related Compounds with Diaryliodonium Salts

Abstract

High Resolution Image Download MS PowerPoint Slide We developed a direct metal-free S- arylation of phosphorothioate diesters using diaryliodonium salts. The method 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 a chalcogen. The reaction proceeds with a full retention of the stereogenic center at the phosphorus atom, opening convenient access to P-chiral products. The mechanism of the reaction was established using DFT calculations.