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Regioselective C–H selenylation of heteroarenes under metal-free conditions

Author(s):

Ricardo F. Schumacher*, Roberta Cargnelutti, Adriane Sperança, Jean C. Kazmierczak, Thiago Anjos, Cleidi M. Hartmann and Benhur Godoi*  

Abstract:


Selenium-containing heteroarenes consist of a synthetically valuable family of compounds that found applications in many different areas, such as organic synthesis, medicinal chemistry, supramolecular chemistry, and optoelectronic devices construction. Over the past decade, many advances have been achieved to the synthesis of these substances, and this review aims to cover a literature survey of the direct selenylation of heteroarenes under metal-free conditions, which represents one of the most powerful synthetic strategies for the preparation of those target molecules. The construction of new C-Se bonds through selective C-H functionalization reactions has become useful and atom-economical. The widespread adoption of metal-free approaches has emerged as versatile, sustainable, and safe access to these organoselenium compounds. Among the features of these new protocols are the use of mild oxidants and halogen-based catalysts, inorganic bases, as well as photo-induced reactions, and electrosynthesis.

Keywords:

C-H Selenylation, heteroarenes, diaryl diselenide, metal-free conditions, electrochemical, visible-light, halogen-based catalysts, mild oxidants.

Affiliation:

Departamento de Química, Universidade Federal de Santa Maria, UFSM, 97105-900 Santa Maria, RS, Departamento de Química, Universidade Federal de Santa Maria, UFSM, 97105-900 Santa Maria, RS, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, UFFS, 97900‐000, Cerro Largo, RS, Departamento de Química, Universidade Federal de Santa Maria, UFSM, 97105-900 Santa Maria, RS, Departamento de Química, Universidade Federal de Santa Maria, UFSM, 97105-900 Santa Maria, RS, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, UFFS, 97900‐000, Cerro Largo, RS, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, UFFS, 97900‐000, Cerro Largo, RS



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