Photocatalytic Oxidative C–H Thiolation: Synthesis of Benzothiazoles and Sulfenylated Indoles
| Autor: | Ashley D. Nguyen, Diane K. Smith, Mario Cedano, Ernesto Millan Aceves, Samuel T. Albright, Jeffrey L. Gustafson, Andrew N. Dinh |
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| Rok vydání: | 2019 |
| Předmět: |
Indole test
010405 organic chemistry Organic Chemistry Cationic polymerization chemistry.chemical_element Photoredox catalysis 010402 general chemistry 01 natural sciences Sulfur Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Nucleophile Benzothiazole chemistry Electrophile Cyclic voltammetry |
| Zdroj: | Synlett. 30:1648-1655 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0039-1690107 |
| Popis: | We report studies on the photocatalytic formation of C–S bonds to form benzothiazoles via an intramolecular cyclization and sulfenylated indoles via an intermolecular reaction. Cyclic voltammetry (CV) and density functional theory studies suggest that benzothiazole formation proceeds via a mechanism that involves an electrophilic sulfur radical, while the indole sulfenylation likely proceeds via a nucleophilic sulfur radical adding into a radical cationic indole. These conditions were successfully extended to several thiobenzamides and indole substrates. |
| Databáze: | OpenAIRE |
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