Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes
| Autor: | Xiaodan Zhao, Jie Luo, Zechen Zhu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Carboxylic acid Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Redox 0104 chemical sciences Catalysis Hydroxylation chemistry.chemical_compound chemistry Selenide Organic chemistry Physical and Theoretical Chemistry Vicinal Selenium Sulfamide |
| Zdroj: | Organic letters. 19(18) |
| ISSN: | 1523-7052 |
| Popis: | A new and efficient method for diaryl selenide catalyzed vicinal CF3S hydroxylation of 1,1-multisubstitued alkenes has been developed. Various trifluoromethylthiolated tertiary alcohols could be readily synthesized under mild conditions. This method is also effective for the intramolecular cyclization of alkenes tethered by carboxylic acid, hydroxy, sulfamide, or ester groups and is associated with the introduction of a CF3S group. Mechanistic studies have revealed that the pathway involves a redox cycle between Se(II) and Se(IV) and Lewis basic selenium catalysis. |
| Databáze: | OpenAIRE |
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