Abstract
Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.
Highlights
Photocatalysis, the use of light to promote organic transformations, is a rather old concept that was first conceived in the early 1900s by Ciamician [1]
Many successful Atom transfer radical addition (ATRA) reactions have been reported in literature, most of which are metal-catalyzed, employing copper, ruthenium, iridium, palladium, or nickel-based complexes [13,14,15,16,17,18]
The synthesis and study of new metal-based complexes that can be employed as photocatalysts is ruthenium-based photoactive complexes [35,36,37,38,39], we present the use of alternative ruthenium-based essential, in order to further expand the substrate scope
Summary
Photocatalysis, the use of light to promote organic transformations, is a rather old concept that was first conceived in the early 1900s by Ciamician [1]. The synthesis and study of new metal-based complexes that can be employed as ATRA reactions with bromoacetonitrile, in the presence of a metal-based catalyst, is rather limited photocatalysts is essential, in order to further expand the substrate scope. We have already contributed to this field with two studies, one focusing on expanding the widen the scope of brominated addition products, the use of other alkyl halides, such as scope of olefins with iridium photocatalysts, just by altering the reaction mechanism utilizing sodium bromotrichloromethane, which is used successfully in ATRA reactions, is required [28,29,30]. The synthesis and study of new metal-based complexes that can be employed as photocatalysts is ruthenium-based photoactive complexes [35,36,37,38,39], we present the use of alternative ruthenium-based essential, in order to further expand the substrate scope.
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