Palladium-Catalyzed Ortho C-H Arylation of Unprotected Anilines
Metal-catalyzed C-H functionalizations on the aryl ring of anilines usually need cumbersome N-protection-deprotection strategies to ensure chemoselectivity. We describe here the Pd-catalyzed direct C-H arylation of unprotected anilines with no competition of the N-arylation product. The ligand [2,2&...
| Autores: | , , , |
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| Tipo de documento: | artigo |
| Data de publicação: | 2022 |
| País: | España |
| Recursos: | Universitat Autònoma de Barcelona |
| Repositório: | Dipòsit Digital de Documents de la UAB |
| Idioma: | inglês |
| OAI Identifier: | oai:ddd.uab.cat:283550 |
| Acesso em linha: | https://ddd.uab.cat/record/283550 https://dx.doi.org/urn:doi:10.1021/acscatal.2c05206 |
| Access Level: | Acceso aberto |
| Palavra-chave: | C-H activation Unprotected anilines Direct arylation Palladium Metal-ligand cooperation Pyridones |
| Resumo: | Metal-catalyzed C-H functionalizations on the aryl ring of anilines usually need cumbersome N-protection-deprotection strategies to ensure chemoselectivity. We describe here the Pd-catalyzed direct C-H arylation of unprotected anilines with no competition of the N-arylation product. The ligand [2,2'-bipyridin]-6(1 H)-one drives the chemoselectivity by kinetic differentiation in the product-forming step, while playing a cooperating role in the C-H cleavage step. The latter is favored in an anionic intermediate where the NH moiety is deprotonated, driving the regioselectivity of the reaction toward ortho substitution. |
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