Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents
| Autor: | Franck Le Vaillant, Jerome Waser, Stefano Nicolai, Alec Gagnebin, Stephanie G. E. Amos |
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| Předmět: |
vinyl sulfoxides
aryl sulfoxides oxidation Alkylation enantioselective arylation 010402 general chemistry 01 natural sciences chemistry.chemical_compound Reactivity (chemistry) hypervalent iodine reagents alkylation Alkyl palladium-catalyzed arylation thiols chemistry.chemical_classification 010405 organic chemistry Aryl Organic Chemistry Enantioselective synthesis asymmetric-synthesis Combinatorial chemistry 0104 chemical sciences chemistry Reagent sulfur Electrophile Organic synthesis |
| Popis: | Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis. |
| Databáze: | OpenAIRE |
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