Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides
| Autor: | Leonardo Degennaro, James A. Bull, Michelle Afonso, Edward L. Briggs, Arianna Tota, Gala Ogalla Estévez, Sahra St John-Campbell, Renzo Luisi |
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| Přispěvatelé: | Engineering & Physical Science Research Council (EPSRC), Engineering & Physical Science Research Council (E, The Royal Society |
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Aryl Organic Chemistry Hypervalent molecule chemistry.chemical_element 010402 general chemistry Iodine 01 natural sciences Biochemistry Product distribution 0104 chemical sciences Sulfonamide chemistry.chemical_compound chemistry Reagent Organic chemistry Ammonium carbamate Physical and Theoretical Chemistry 03 Chemical Sciences |
| Zdroj: | Organic Letters. 20:2599-2602 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.8b00788 |
| Popis: | Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products. |
| Databáze: | OpenAIRE |
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