Enantioselective Friedel-Crafts alkylation of 1,3,5-trimethoxybenzene with trans-ß-nitrostyrenes catalysed by [Cp*Rh{(R)-Prophos}(H2O)][SbF6]2 (Prophos = propane-1,2-diyl-bis(diphenylphosphane)
Cored, Jorge ; Sánchez, Antonio ; Viguri, Fernando (Universidad de Zaragoza) ; Rodríguez, Ricardo ; Lamata, Pilar (Universidad de Zaragoza) ; Carmona, Daniel![Enantioselective Friedel-Crafts alkylation of 1,3,5-trimethoxybenzene with trans-ß-nitrostyrenes catalysed by [Cp*Rh{(R)-Prophos}(H2O)][SbF6]2 (Prophos = propane-1,2-diyl-bis(diphenylphosphane)](https://zaguan.unizar.es/record/145111/files/texto_completo.jpg?subformat=icon)
Resumen: The aqua complex (SRh,RC)-[Cp*Rh{(R)-Prophos}(H2O)][SbF6]2 (Prophos = propane-1,2-diyl-bis(diphenylphosphane) catalyses the asymmetric Friedel-Crafts (FC) alkylation of 1,3,5-trimethoxybenzene with trans-β-nitrostyrenes. Only the monoalkylated adduct was obtained in all cases with enantioselectivities of up to 93/7 e.r. Solution NMR measurements have allowed us to detect and characterise catalytic intermediates such as metal-trans-β-nitrostyrene and metal‑aci-nitro complexes, as well as free aci‑nitro compound. Based on these studies, a Michael-type Friedel-Crafts mechanism is proposed.
Idioma: Inglés
DOI: 10.1016/j.jorganchem.2024.123377
Año: 2024
Publicado en: Journal of Organometallic Chemistry 1021 (2024), 123377 [13 pp.]
ISSN: 0022-328X
Factor impacto JCR: 2.4 (2024)
Categ. JCR: CHEMISTRY, ORGANIC rank: 21 / 57 = 0.368 (2024) - Q2 - T2
Categ. JCR: CHEMISTRY, INORGANIC & NUCLEAR rank: 22 / 42 = 0.524 (2024) - Q3 - T2
Factor impacto SCIMAGO: 0.385 - Biochemistry (Q3) - Inorganic Chemistry (Q3) - Physical and Theoretical Chemistry (Q3) - Organic Chemistry (Q3) - Materials Chemistry (Q3)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E05-23R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-AEI-FEDER/PID2021-122406NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MCIU/CTQ2018-095561-BI00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes.
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Idioma: Inglés
DOI: 10.1016/j.jorganchem.2024.123377
Año: 2024
Publicado en: Journal of Organometallic Chemistry 1021 (2024), 123377 [13 pp.]
ISSN: 0022-328X
Factor impacto JCR: 2.4 (2024)
Categ. JCR: CHEMISTRY, ORGANIC rank: 21 / 57 = 0.368 (2024) - Q2 - T2
Categ. JCR: CHEMISTRY, INORGANIC & NUCLEAR rank: 22 / 42 = 0.524 (2024) - Q3 - T2
Factor impacto SCIMAGO: 0.385 - Biochemistry (Q3) - Inorganic Chemistry (Q3) - Physical and Theoretical Chemistry (Q3) - Organic Chemistry (Q3) - Materials Chemistry (Q3)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E05-23R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-AEI-FEDER/PID2021-122406NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MCIU/CTQ2018-095561-BI00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. Exportado de SIDERAL (2025-09-22-14:47:03)
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Record created 2024-09-26, last modified 2025-09-23