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Levy, Jeffrey N; Alegre-Requena, Juan V; Liu, Renrong; Paton, Robert S; McNally, Andrew
Journal of the American Chemical Society, 06/2020, Letnik: 142, Številka: 25Journal Article
Halopyridines are key building blocks for synthesizing pharmaceuticals, agrochemicals, and ligands for metal complexes, but strategies to selectively halogenate pyridine C–H precursors are lacking. We designed a set of heterocyclic phosphines that are installed at the 4-position of pyridines as phosphonium salts and then displaced with halide nucleophiles. A broad range of unactivated pyridines can be halogenated, and the method is viable for late-stage halogenation of complex pharmaceuticals. Computational studies indicate that C–halogen bond formation occurs via an S N Ar pathway, and phosphine elimination is the rate-determining step. Steric interactions during C–P bond cleavage account for differences in reactivity between 2- and 3-substituted pyridines.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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in: SICRIS
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