Rhodium-Catalyzed Oxidative Alkenylation of Anisole : Control of Regioselectivity
© 2024 The Authors. Published by American Chemical Society.
| Veröffentlicht in: | Organometallics. - 1998. - 43(2024), 12 vom: 24. Juni, Seite 1362-1376 |
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| Format: | Online-Aufsatz |
| Sprache: | English |
| Veröffentlicht: |
2024
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| Zugriff auf das übergeordnete Werk: | Organometallics |
| Schlagworte: | Journal Article |
| Zusammenfassung: | © 2024 The Authors. Published by American Chemical Society. We report the conversion of anisoles and olefins to alkenyl anisoles via a transition-metal-catalyzed arene C-H activation and olefin insertion mechanism. The catalyst precursor, [(η2-C2H4)2Rh(μ-OAc)]2, and the in situ oxidant Cu(OPiv)2 (OPiv = pivalate) convert anisoles and olefins (ethylene or propylene) to alkenyl anisoles. When ethylene is used as the olefin, the o/m/p ratio varies between approximately 1:3:1 (selective for 3-methoxystyrene) and 1:5:10 (selective for 4-methoxystyrene). When propylene is the olefin, the o/m/p regioselectivity varies between approximately 1:8:20 and 1:8.5:5. The o/m/p ratios depend on the concentration of pivalic acid and olefin. For example, when using ethylene, at relatively high pivalic acid concentrations and low ethylene concentrations, the o/m/p regioselectivity is 1:3:1. Conversely, again for use of ethylene, at relatively low pivalic acid concentrations and high ethylene concentrations, the o/m/p regioselectivity is 1:5:10. Mechanistic studies of the conversion of anisoles and olefins to alkenyl anisoles provide evidence that the regioselectivity is likely under Curtin-Hammett conditions |
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| Beschreibung: | Date Revised 29.06.2024 published: Electronic-eCollection Citation Status PubMed-not-MEDLINE |
| ISSN: | 0276-7333 |
| DOI: | 10.1021/acs.organomet.4c00155 |