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240628s2024 xx |||||o 00| ||eng c |
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|a 10.1021/acs.organomet.4c00155
|2 doi
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|a eng
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| 100 |
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|a Reid, Christopher W
|e verfasserin
|4 aut
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| 245 |
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|a Rhodium-Catalyzed Oxidative Alkenylation of Anisole
|b Control of Regioselectivity
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|c 2024
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|a Text
|b txt
|2 rdacontent
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|a ƒaComputermedien
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|2 rdamedia
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| 338 |
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|a ƒa Online-Ressource
|b cr
|2 rdacarrier
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|a Date Revised 29.06.2024
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|a published: Electronic-eCollection
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|a Citation Status PubMed-not-MEDLINE
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| 520 |
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|a © 2024 The Authors. Published by American Chemical Society.
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|a 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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| 650 |
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|a Journal Article
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|a Gunnoe, T Brent
|e verfasserin
|4 aut
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| 773 |
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|i Enthalten in
|t Organometallics
|d 1998
|g 43(2024), 12 vom: 24. Juni, Seite 1362-1376
|w (DE-627)NLM098167103
|x 0276-7333
|7 nnas
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| 773 |
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|g volume:43
|g year:2024
|g number:12
|g day:24
|g month:06
|g pages:1362-1376
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| 856 |
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|u http://dx.doi.org/10.1021/acs.organomet.4c00155
|3 Volltext
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