Zeolites Catalyze the Nazarov Reaction and the tert-Butylation of Alcohols by Stabilization of Carboxonium Intermediates

María Tejeda-Serrano; Sergio Sanz-Navarro; Finn Blake; Antonio Leyva-Pérez

doi:10.1055/s-0039-1690896

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(14): 2031-2037
DOI: 10.1055/s-0039-1690896

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Zeolites Catalyze the Nazarov Reaction and the tert-Butylation of Alcohols by Stabilization of Carboxonium Intermediates

María Tejeda-Serrano

,

Sergio Sanz-Navarro

,

Finn Blake

,

Antonio Leyva-Pérez ∗

Instituto de Tecnología Química, Universidad Politècnica de València, Consejo Superior de Investigaciones Científicas (ITQ, UPV-CSIC), Avda. de los Naranjos s/n, 46022 Valencia, Spain eMail: anleyva@itq.upv.es

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Abstract

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Abstract

Zeolites are the most used catalysts worldwide in petrochemistry processes, with particular ability to stabilize carbocations. However, the use of zeolites in organic synthesis is still scarce. We show here that representative carboxonium-mediated organic reactions, such as the Nazarov cyclization and the tert-butylation of alcohols with tert-butyl acetate, typically performed with very strong acid catalysts in solution such as triflic acid, can be catalyzed by simple zeolites with high yield and selectivity. The aluminosilicate framework stabilizes the intermediate carboxonium species and overrides the need for superacid protons in solution.

Key words

zeolites - solid catalyst - Nazarov reaction - tert-butylation reaction - carboxonium - heterogeneous catalysis

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