Copper‐Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction
1H‐Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by TpxCu complexes (Tpx=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the C...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2020 |
| País: | España |
| Institución: | Universidad de Huelva (UHU) |
| Repositorio: | Arias Montano. Repositorio Institucional de la Universidad de Huelva |
| Idioma: | inglés |
| OAI Identifier: | oai:ariasmontano.uhu.es:10272/19646 |
| Acceso en línea: | http://hdl.handle.net/10272/19646 |
| Access Level: | acceso abierto |
| Palabra clave: | Pyrrole functionalization Copper catalysis Carbene transfer Diazo compounds C-H functionalization Selectivity 23 Química |
| Sumario: | 1H‐Pyrroles can be directly functionalized by means of the incorporation of carbene groups from diazo compounds, in a process catalyzed by TpxCu complexes (Tpx=hydrotrispyrazolylborate ligand). The reactions take place with a complete selectivity toward the formal insertion of the carbene into the Cα−H bond, leading to alkylated pyrroles, with no modification of the Cβ−H, N−H or C=C bonds of the pyrrole unit. Alkyl substituents at C‐ring as well as alkyl, aryl, allyl or alkyne substitution at N atom are tolerated, the strategy affording 20 new pyrrole derivatives. The observance of partial deuteration at the methylene group when the reaction is carried out with added D2O serves to discard the direct insertion of the carbene group into the Csp2−H bond, the alternative electrophilic attack to the pyrrole ring being feasible. |
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