Phototriggered Fluoroalkylation/Cyclization of Unactivated 1-Acryloyl-2-cyanoindoles: Synthesis of RCOCF<sub>2</sub>-Substituted Pyrrolo[1,2-<i>a</i>]indolediones
Weixian Lv, Pengyuan Yang, Jinwei Yuan, Jiayi Li, Mengran Liang, Yitong Liu, Dongliang Xing, Liangru Yang
Abstract
A photochemical approach toward RCOCF 2 -substituted pyrrolo[1,2- a ]indolediones was developed by the radical cascade difluoroalkylation/cyclization reaction of unactivated 1-acryloyl-2-cyanoindoles with ethyl iododifluoroacetate or iododifluoramides under visible-light irradiation. This transition-metal- and photosensitizer-free protocol afforded diverse difluoroalkylated pyrrolo[1,2- a ]indolediones in moderate to good yields under mild reaction conditions. Most appealingly, the reaction can proceed smoothly under sunlight irradiation, which opens a new avenue toward difluoroalkylated pyrrolo[1,2- a ]indolediones.
Topics & Concepts
ChemistryPhotosensitizerPhotochemistryIrradiationCascade reactionCascadeReaction conditionsCombinatorial chemistryOrganic chemistryCatalysisChromatographyPhysicsNuclear physicsFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds