A General Copper/Manganese Cocatalyzed C-H Selenation of Arenes, Heteroarenes, and Alkenes under Air
| Autor: | Gurupada Bairy, Bijaya Kumar Singh, Ranjan Jana |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
8-Aminoquinoline
010405 organic chemistry Chemistry chemistry.chemical_element General Chemistry Manganese 010402 general chemistry 01 natural sciences Combinatorial chemistry Copper 0104 chemical sciences Catalysis chemistry.chemical_compound Nucleophile Organic chemistry Chelation Stereoselectivity Stoichiometry |
| Zdroj: | ChemistrySelect. 2:9227-9232 |
| ISSN: | 2365-6549 |
| DOI: | 10.1002/slct.201701758 |
| Popis: | Despite significant progress, copper-catalyzed, directed C−H activation to form C-heteroatom bond is a challenging problem due to strong chelation with the directing group and the incoming nucleophile. Therefore, stoichiometric copper salt was used which is not practical from industrial standpoint. Here we have developed a copper-manganese dual catalytic system for a general chelation-assisted C(sp2)-H selenation of benzamides and acrylamides. Interestingly, the acrylamides provided thermodynamically unfavourable (Z)-vinyl selenides with complete control of regio- and stereoselectivity. In addition, reaction with selenium powder in lieu of diorganyldiselenide provided the cyclic ebselen derivatives via C−Se/N−Se bond formation cascade. Thus, we provide here a practical and user-friendly protocol for C(sp2)-H selenation combining inexpensive first row-transition metal catalysts coupled with aerial oxygen as the terminal oxidant. |
| Databáze: | OpenAIRE |
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