Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

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Rodrigues Jr, Manoel T. ; de Oliveira, Aline S. B. ; Gomes, Ralph C. ; Hirata, Amanda Soares ; Zeoly, Lucas A. ; Santos, Hugo ; Arantes, Joao ; Reis-Silva, Catarina Sofia Mateus ; Machado-Neto, Joao Agostinho ; Costa-Lotufo, Leticia Veras ; Coelho, Fernando

• Document type: Journal article
• Source: Beilstein Journal of Organic Chemistry; v. 20, p. 12-pg., 2024-05-21.

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-ethoxycarbonyl-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 distinct product classes (3-aryl-2ethoxycarbonyl-1-indanones and 3-aryl-1-indanones) in good to excellent yield. The reaction did not require additives and was insensitive to both air and moisture. Preliminary biological evaluation of some indanones showed a promising profile against some human cancer line cells. (AU)

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