Bismuth(III) Triflate: An Economical and Environmentally Friendly Catalyst for the Nazarov Reaction

Manoel Trindade Rodrigues Jr.; Aline Silva Barroso de Oliveira; Ralph da Costa Gomes; Amanda Soares Hirata; Lucas A Zeoly; Hugo Santos; João Arantes; Catarina Sofia Mateus Reis-Silva; João Agostinho Machado-Neto; Leticia Veras Costa-Lotufo; Fernando Coelho

doi:10.3762/bxiv.2024.1.v1

Bismuth(III) Triflate: An Economical and Environmentally Friendly Catalyst for the Nazarov Reaction

Manoel Trindade Rodrigues Jr. ,
Aline Silva Barroso de Oliveira ,
Ralph da Costa Gomes ,
Amanda Soares Hirata ,
Lucas A Zeoly ,
Hugo Santos ,
João Arantes ,
Catarina Sofia Mateus Reis-Silva ,
João Agostinho Machado-Neto ,
Leticia Veras Costa-Lotufo and
Fernando Coelho

Submitting author affiliation:

University of Campinas, Campinas, Brazil

Beilstein Arch. 2024, 20241. https://doi.org/10.3762/bxiv.2024.1.v1

Published 03 Jan 2024

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SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

We describe the use of bismuth (III) triflate as an efficient and environmentally friendly catalyst for the Nazarov reaction of aryl vinyl ketones, leading to the synthesis of 3-aryl-2-carboethoxy-1-indanones and 3-aryl-1-indanones. By changing the temperature and reaction time, it was possible to modulate the reactivity, allowing the synthesis of two different products in good to excellent yields (3-aryl-2-carboethoxy-1-indanones and 3-aryl-2-carbethoxy-1-indanones). The reaction does not need additives and is insensitive to both air and moisture. The preliminary biological evaluation of some indanones show a promissory profile against some human cancer line cells.

Keywords: Indanones; Heterocycles; Nazarov reaction; Bismuth; Catalysis

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Rodrigues Jr., M. T.; de Oliveira, A. S. B.; Gomes, R. D. C.; Hirata, A. S.; Zeoly, L. A.; Santos, H.; Arantes, J.; Reis-Silva, C. S. M.; Machado-Neto, J. A.; Costa-Lotufo, L. V.; Coelho, F. Beilstein Arch. 2024, 20241. doi:10.3762/bxiv.2024.1.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)