Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach

GABRIELA OKSDATH MANSILLA*

ORGANIC PROCESS RESEARCH & DEVELOPMENT

AMER CHEMICAL SOC

Lugar: Washington; Año: 2020

1083-6160

he potential application of multistep continuous-flow systems has had a great impact on the syntheses of activepharmaceutical ingredients, natural products, and commodity chemicals. In this report, the highly efficient combination of a chemicalreduction and a photochemical Csp2−H activation reaction for selenylation of biologically relevant electron-rich arenes was achievedby means of a continuous-flow process. First, the reduction of alkyl and aryl selenocyanates by Rongalite was achieved giving thecorresponding diselenides; second, the photoactivation of the Se−Se bond resulted in the selenylation of electron-rich arenes, bothsteps from good to excellent yields. In all cases, the reaction time was shortened, and isolated yields were improved when comparedto batch reaction conditions. Furthermore, connecting both reactions in a multistep continuous-flow sequence was possible evenwhen reductive and photooxidative transformations were coupled.