Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles...
| Authors: | , , , |
|---|---|
| Format: | article |
| Publication Date: | 2020 |
| Country: | España |
| Institution: | Universidad de Huelva (UHU) |
| Repository: | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| Language: | English |
| OAI Identifier: | oai:ariasmontano.uhu.es:10272/19698 |
| Online Access: | http://hdl.handle.net/10272/19698 |
| Access Level: | Open access |
| Keyword: | Nitrene transfer Pyrrole functionalization C-H amidation Copper catalysis Copper nitrene 23 Química |
| Summary: | The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5‐tribromo‐pyrazolyl)borate). N‐substituted pyrroles also verify the same transformation. The mechanism proposal is similar to that previously described for benzene amidation with the same catalyst and PhI=NTs, which takes place through aziridine formation, ring opening and 1,2‐hydrogen shift. A cascade reaction involving the coupling of 2,5‐dimethylfuran, 1,2,3‐trimethyl‐pyrrole and a nitrene NTs group is also described, leading to a 1,2‐dihydropyridine‐imine compound. |
|---|