Visible Light and Triselenium Dicyanide (TSD): New Horizons in the Synthesis of Organic Selenocyanates

• Published in: Chemistry : a European journal Vol. 29; no. 59; p. e202301934
• Main Authors: Anghinoni, Joao M., Ferreira, Sabrina S., Piquini, Paulo C., Iglesias, Bernardo A., Perin, Gelson, Penteado, Filipe, Lenardao, Eder J.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 23.10.2023; Wiley Subscription Services, Inc
• Subjects: Alkenes; Carbonyl compounds; Carbonyls; Chemistry; Chemistry, Multidisciplinary; Irradiation; Light irradiation; Oxidation; Physical Sciences; Science & Technology; Styrene; Styrenes; Synthesis; ALPHA-(PHENYLSELANYL) ACETOPHENONE; visible light; triselenium dicyanide (TSD); carbonyl selenocyanate; ORGANOSELENIUM; INHIBITION; ANTIOXIDANT; TRANSITION-METAL; GREEN CHEMISTRY; EBSELEN; arylimidazopyridines; SUSTAINABLE DEVELOPMENT GOALS; DERIVATIVES; EXPLORING GREEN; 2-arylimidazo[1,2-a] pyridines; α-carbonyl selenocyanate
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.202301934

Herein, we describe a new method for the synthesis of & alpha;-carbonyl selenocyanates by reacting triselenium dicyanide (TSD) and styrenes under blue light irradiation and O2 atmosphere. The reactions are triggered by the formation of Se-centered radical species, followed by the addition/oxidation of the styrene & pi;-bond. & alpha;-Carbonyl selenocyanates and & alpha;-hydroxy selenocyanates were obtained in moderate to excellent yields from aryl- and alkyl-substituted alkenes, respectively. It was demonstrated that & alpha;-carbonyl selenocyanates could be used as a synthetic platform in a multicomponent reaction strategy to prepare 2-phenylimidazo[1,2-a]pyridine derivatives, which were evaluated for their photophysical properties. Overall, this new method provides a useful tool for synthesizing & alpha;-carbonyl selenocyanates, and demonstrates their potential for use in the synthesis of other compounds, thus giving new synthetic opportunities to construct organic selenocyanate compounds. An ingenious method for the synthesis of & alpha;-carbonyl selenocyanates and & alpha;-hydroxy selenocyanates is to simply react triselenium dicyanide and styrenes (or alkenes) under blue light irradiation and O2. Additionally, & alpha;-carbonyl selenocyanates were explored as a synthetic platform in a multicomponent process to prepare 2-phenylimidazo[1,2-a]pyridine derivatives, which were investigated for their photophysical properties.image