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Ruthenium-Catalyzed Monoselective C-H Methylation and d 3-Methylation of Arenes.
| Content Provider | Europe PMC |
|---|---|
| Author | Hogg, Ashley Wheatley, Matthew Domingo-Legarda, Pablo Carral-Menoyo, Asier Cottam, Naomi Larrosa, Igor |
| Copyright Year | 2022 |
| Abstract | Site-selective installation of C–Me bonds remainsa powerfuland sought-after tool to alter the chemical and pharmacological propertiesof a molecule. Direct C–H functionalization provides an attractivemeans of achieving this transformation. Such protocols, however, typicallyutilize harsh conditions and hazardous methylating agents with poorapplicability toward late-stage functionalization. Furthermore, highlymonoselective methylation protocols remain scarce. Herein, we reportan efficient monoselective, directed ortho-methylationof arenes using N,N,N-trimethylanilinium salts asnoncarcinogenic, bench-stable methylating agents. We extend this protocolto d3-methylation in addition to the late-stagefunctionalization of pharmaceutically active compounds. Detailed kineticstudies indicate the rate-limiting in situ formation of MeI is integralto the observed reactivity. |
| Related Links | https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC9709947&blobtype=pdf |
| Journal | JACS Au |
| Volume Number | 2 |
| DOI | 10.1021/jacsau.2c00399 |
| PubMed Central reference number | PMC9709947 |
| Issue Number | 11 |
| PubMed reference number | 36465534 |
| e-ISSN | 26913704 |
| Language | English |
| Publisher | American Chemical Society |
| Publisher Date | 2022-10-21 |
| Access Restriction | Open |
| Rights License | Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). © 2022 The Authors. Published by American Chemical Society |
| Subject Keyword | catalysis ruthenium methylation C−H activation late-stage functionalization ammonium salts |
| Content Type | Text |
| Resource Type | Article |
| Subject | Chemistry Physical and Theoretical Chemistry Analytical Chemistry Organic Chemistry |