{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Mondal S"],"funding":["Stiftelsen Olle Engkvist Byggmästare","Vetenskapsrådet"],"pagination":["e202216296"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10108051"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["62(8)"],"pubmed_abstract":["Efficient protocols for accessing iodo-substituted diaryl and aryl(vinyl) sulfides have been developed using iodonium salts as reactive electrophilic arylation and vinylation reagents. The reactions take place under transition-metal-free conditions, employing odorless and convenient sulfur reagents. A wide variety of functional groups are tolerated in the S-diarylation, enabling the regioselective late-stage application of several heterocycles and drug molecules under mild reaction conditions. A novel S-difunctionalization pathway was discovered using vinyliodonium salts, which proceeds under additive-free reaction conditions and grants excellent stereoselectivity in the synthesis of aryl(vinyl) sulfides. A one-pot strategy combining transition-metal-free diarylation and subsequent reduction provided facile access to electron-rich thioanilines and a direct synthesis of a potential drug candidate derivative. The retained iodo group allows a wide array of further synthetic transformations. Mechanistic insights were elucidated by isolating the key intermediate, and the relevant energy profile was substantiated by DFT calculations."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Transition-Metal-Free Difunctionalization of Sulfur Nucleophiles."],"pmcid":["PMC10108051"],"funding_grant_id":["2019-04232","207-0615"],"pubmed_authors":["Mondal S","Olofsson B","Di Tommaso EM"],"additional_accession":[]},"is_claimable":false,"name":"Transition-Metal-Free Difunctionalization of Sulfur Nucleophiles.","description":"Efficient protocols for accessing iodo-substituted diaryl and aryl(vinyl) sulfides have been developed using iodonium salts as reactive electrophilic arylation and vinylation reagents. The reactions take place under transition-metal-free conditions, employing odorless and convenient sulfur reagents. A wide variety of functional groups are tolerated in the S-diarylation, enabling the regioselective late-stage application of several heterocycles and drug molecules under mild reaction conditions. A novel S-difunctionalization pathway was discovered using vinyliodonium salts, which proceeds under additive-free reaction conditions and grants excellent stereoselectivity in the synthesis of aryl(vinyl) sulfides. A one-pot strategy combining transition-metal-free diarylation and subsequent reduction provided facile access to electron-rich thioanilines and a direct synthesis of a potential drug candidate derivative. The retained iodo group allows a wide array of further synthetic transformations. Mechanistic insights were elucidated by isolating the key intermediate, and the relevant energy profile was substantiated by DFT calculations.","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Feb","modification":"2025-04-26T04:58:21.173Z","creation":"2025-04-06T11:21:55.496Z"},"accession":"S-EPMC10108051","cross_references":{"pubmed":["36546892"],"doi":["10.1002/anie.202216296"]}}