Ruthenium-Catalyzed Monoselective C–H Methylation and d3-Methylation of Arenes
| Autor: | Ashley Hogg, Matthew Wheatley, Pablo Domingo-Legarda, Asier Carral-Menoyo, Naomi Cottam, Igor Larrosa |
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| Rok vydání: | 2022 |
| Zdroj: | Hogg, A, Wheatley, M, Domingo Legarda, P, Carral-Menoyo, A, Cottam, N & Larrosa, I 2022, ' Ruthenium-Catalyzed Mono-Selective C–H Methylation and d 3-Methylation of Arenes ', JACS Au . https://doi.org/10.1021/jacsau.2c00399 JACS Au |
| ISSN: | 2691-3704 |
| Popis: | Site-selective installation of C–Me bonds remains a powerful and sought-after tool to alter the chemical and pharmacological properties of a molecule. Direct C–H functionalization provides an attractive means of achieving this transformation. Such protocols, however, typically utilize harsh conditions and hazardous methylating agents with poor applicability towards late-stage functionalization. Furthermore, highly mono-selective methylation protocols remain scarce. Herein, we report an efficient mono-selective, directed ortho-methylation of arenes using N,N,N-trimethylanilinium salts as a non-carcinogenic, bench-stable methylating agents. We extend this protocol to d3-methylation, in addition to the late-stage functionalization of pharmaceutically active compounds. Detailed kinetic studies indicate the rate-limiting insitu formation of MeI as integral to the observed reactivity. |
| Databáze: | OpenAIRE |
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