Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences

William H. García-Santos, Javier Ordóñez-Hernández, Mónica Farfán-Paredes, Hiram M. Castro-Cruz, Norma A. Macías-Ruvalcaba, Norberto Farfán and Alejandro Cordero-Vargas*

*Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Coyoacán, C.P., México, D.F. 04510, México, Email: acorderounam.mx

W. H. García-Santos, J. Ordóñez-Hernández, M. Farfán-Paredes, H. M. Castro-Cruz, N. A. Macías-Ruvalcaba, N. Farfán, A. Cordero-Vargas, J. Org. Chem., 2021, 86, 16315-16326.

DOI: 10.1021/acs.joc.1c01598

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Abstract

Dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is an organic photocatalyst with similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)₃Cl₂, commonly used in radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. BODIPY also catalyzes syntheses of γ-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans.

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Visible-Light Photocatalytic Preparation of 1,4-Ketoaldehydes and 1,4-Diketones from α-Bromoketones and Alkyl Enol Ethers

W. H. García-Santos, H. B. Mateus-Ruiz, A. Cordero-Vargas, Org. Lett., 2019, 21, 4092-4096.

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Key Words

1,4-dicarbonyl compounds, organocatalysis, photochemistry

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ID: J42-Y2021