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Metal-Free S-Arylation of Phosphorothioate Diesters and Related Compounds with Diaryliodonium Salts.

ABSTRACT: 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.

SUBMITTER: Sarkar S

PROVIDER: S-EPMC9903330 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Metal-Free S-Arylation of Phosphorothioate Diesters and Related Compounds with Diaryliodonium Salts.

Sarkar Sudeep S Kalek Marcin M

Organic letters 20230120 4

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-ch ...[more]

PMID: 36662120

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