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Visible‐Light‐Enabled Trifluoromethylative Pyridylation of Alkenes from Pyridines and Triflic Anhydride

Kangjae Lee, Seojin Lee, Nam Hoon Kim, Seonyul Kim, Sungwoo Hong

2020Angewandte Chemie International Edition93 citationsDOI

Abstract

Abstract A general strategy for visible‐light‐enabled site‐selective trifluoromethylative pyridylation of unactivated alkenes has been developed using pyridines and triflic anhydride (Tf 2 O). Intriguingly, the N‐triflylpyridinium salts, generated in situ from pyridines and Tf 2 O, serve as effective modular bifunctional reagents to install both CF 3 and pyridyl groups to various olefins while controlling C4‐selectivity in radical addition to the pyridine core. This synthetic route exhibited broad substrate scope under metal‐free and mild photocatalytic conditions, granting efficient access to valuable C4‐alkylated pyridines and quinolines without requiring prefunctionalization of the reaction site.

Topics & Concepts

ChemistryBifunctionalReagentAnnulationPyridineCombinatorial chemistryOrganic chemistryAlkylationSelectivityCatalysisFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods