Novas metodologias para a síntese de selenetos de diarila usando-se anilinas ou sais de arenodiazônio

Abstract

In this work were developed two methodologies for the synthesis of diaryl selenides. The first methodology describe the reaction of arenediazonium salts 2 with arylselenols, generated in situ by reaction between a diaryl disselenides 1, hypophosphorous acid (H3PO2 – 50 wt% in water), using THF as solvent. The reaction occurred at room temperature under N2. A range of diaryl selenides was synthesized in good yield (63-80%) (Scheme 1). In the second methodology was developed the arylselenation of anilines by direct coupling reaction of diaryl disselenides 1 with anilines 3 in the presence of CuI (3 mol%) and DMSO at 110 °C in air. Through this method, different selanylanilines were obtained with good yields (46-93%) and excellent selectivity (Scheme 2).