Visible Light-Promoted C–C Bond Formation from Hydroxyaryls in Water
Dafne Saporito A , Sergio A. Rodriguez B and Maria T. Baumgartner A CA INFIQC – Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
B CONICET, Instituto de Ciencias Químicas, Facultad de Agronomía y Agroindustrias, Universidad Nacional de Santiago del Estero, Av. Belgrano Sur 1912, Santiago del Estero 4200, Argentina.
C Corresponding author. Email: tere@fcq.unc.edu.ar
Australian Journal of Chemistry 72(12) 978-982 https://doi.org/10.1071/CH19378
Submitted: 5 August 2019 Accepted: 7 October 2019 Published: 8 November 2019
Abstract
An eco-friendly and direct arylation of hydroxyaryls in water using photoinduced reactions with different substrates (1-bromo-2-naphthol, 1-iodo-2-naphthol, N-(2-iodophenyl)acetamide, 5-bromouracil, 2-iodo-N-methylbenzamide, and 2-iodobenzamide) was studied. For example, π-expanded coumarins, compounds with potential optical applications, were synthesized in very high yield, without the use of toxic reagents, in a one-pot reaction. In addition, we demonstrate that the irradiation source (halogen lamp) can be efficiently replaced by an LED without altering the reaction yield.
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