Abstract
AbstractWe report a C(sp3)−C(sp3) cross‐coupling of alkyl bromides and alkyl chlorides with ethers by dual photoredox‐nickel catalysis. The catalytic system comprises of the organic photocatalyst 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4‐CzIPN) and bench stable nickel (II) acetylacetonate in the presence of visible‐light, providing the coupling products in up to 92% yield. Preliminary mechanistic studies suggest two catalytic cycles, as well as the photogeneration of bromine or chlorine radicals from halide atoms that are present in the structures of the coupling partners. The halide radical mediates the hydrogen atom transfer event, avoiding the need of an additional HAT catalyst.magnified image
Highlights
Preliminary mechanistic studies suggest two catalytic cycles, as well as the photogeneration of bromine or chlorine radicals from halide atoms that are present in the structures of the coupling partners
Transition-metal-catalysed cross-coupling reactions are a key technology that has enabled the formation of carbon-carbon bonds between specific coupling partners.[1]
For CÀ H functionalization processes, hydrogen atom transfer (HAT) agents are crucial for generating alkyl radicals.[11]
Summary
Transition-metal-catalysed cross-coupling reactions are a key technology that has enabled the formation of carbon-carbon bonds between specific coupling partners.[1]. CzIPN) and bench stable nickel (II) acetylacetonate in the presence of visible-light, providing the coupling products in up to 92% yield. Metallaphotoredox systems generally employ nickel complexes as transition metal catalysts, as well as organic or metallic photocatalysts.[5] The electropositive nature of nickel favours oxidative addition of alkyl and aryl halides.[10] Nickel-catalyzed reactions proceed through polar and radical mechanisms, where different nickel oxidation states can be achieved.
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