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

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 / 43 = 0.512 (2024) - Q3 - T2

Factor impacto CITESCORE: 4.1 - Inorganic Chemistry (Q2) - Materials Chemistry (Q2) - Biochemistry (Q3) - Organic Chemistry (Q3) - Physical and Theoretical Chemistry (Q3)

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)