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Ir(iii)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents
Transition-metal-catalyzed C–H alkylation reactions directed by aldehydes or ketones have been largely restricted to electronically activated alkenes. Herein, we report a general protocol for the Ir(iii)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents as the...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6301268/ https://www.ncbi.nlm.nih.gov/pubmed/30647887 http://dx.doi.org/10.1039/c8sc03606c |
Sumario: | Transition-metal-catalyzed C–H alkylation reactions directed by aldehydes or ketones have been largely restricted to electronically activated alkenes. Herein, we report a general protocol for the Ir(iii)-catalyzed ortho C–H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents as the coupling partner. Featuring aniline as an inexpensive catalytic ligand, the method was compatible with a wide variety of benzaldehydes, heterocyclic aldehydes, potassium alkyltrifluoroborates as well as a few α,β-unsaturated aldehydes. An X-ray crystal structure of a benzaldehyde ortho C–H iridation intermediate was also successfully obtained. |
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