ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Selenium species-catalyzed biomimetic halogenations of aromatic and heteroaromatic compounds

Bruno H. Rita, Miriam Uemi, and Cristiano Raminelli

Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema, Brazil

E-mail: raminelli@unifesp.br

Received: 7 April 2024  Accepted: 17 June 2024

Abstract:

Herein, we report our investigations on the biomimetic bromofunctionalization of aromatic and heteroaromatic compounds using NaBr as a source of bromine, 30% (w/v) H₂O₂ as an oxidant, and SeCl₄ as a commercially available catalyst in water without a co-solvent. Under these mild conditions, brominated (hetero)aromatic compounds were obtained in reasonable yields. In addition, ⁷⁷Se NMR experiments were performed to provide experimental support for the proposed mechanism of the developed halofunctionalization reaction.

Graphical abstract

Keywords: Environmental Chemistry; Biomimetic synthesis; Bromofunctionalization; Selenium catalysis; Aqueous reaction

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03579-z

Chemical Papers 78 (12) 6971–6977 (2024)