2010
DOI: 10.1590/s0103-50532010000900012
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Abstract: Pd/C catalisa a reação de acoplamento entre 2,4-diiodoquinolina e alquinos terminais em água, proporcionando uma síntese prática, de uma etapa, de 2,4-dialquinilquinolinas. Uma série de derivados de quinolinas relacionadas foi preparada em bons a excelentes rendimentos, usando esta metodologia baseada em água. O uso de outros catalisadores de paládio e solventes foi examinado e o mecanismo de reação discutido.Pd/C facilitated dual C-C bond forming reaction between 2,4-diiodoquinoline and terminal alkynes in wa… Show more

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“…Palladium–CuI‐catalyzed Sonogashira cross‐coupling of 2,4‐dichloroquinoline 34 with excess terminal alkynes afforded the corresponding 2,4‐dialkynylquinolines 35 in a single‐pot operation (Scheme 10) [50]. A Pd/C–CuI‐mediated dual carbon–carbon bond formation reaction of 2,4‐diiodoquinoline with terminal alkynes including propagyl alcohols was achieved in water to afford series of 2,4‐(dialkynyl)quinoline derivatives [51].…”
Section: Application Of Cross‐coupling Reactions In the Synthesis Of mentioning
confidence: 99%
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“…Palladium–CuI‐catalyzed Sonogashira cross‐coupling of 2,4‐dichloroquinoline 34 with excess terminal alkynes afforded the corresponding 2,4‐dialkynylquinolines 35 in a single‐pot operation (Scheme 10) [50]. A Pd/C–CuI‐mediated dual carbon–carbon bond formation reaction of 2,4‐diiodoquinoline with terminal alkynes including propagyl alcohols was achieved in water to afford series of 2,4‐(dialkynyl)quinoline derivatives [51].…”
Section: Application Of Cross‐coupling Reactions In the Synthesis Of mentioning
confidence: 99%
“…The high reactivity at C‐2 versus C‐4 when X = Cl is attributed to the increased positive character of the α‐carbon of the α,β‐unsaturated framework due to the electron‐withdrawing effect of the adjacent nitrogen of the quinoline ring. The observed regioselectivity in alkynylation of 2,4‐dihaloquinolines (X = I, Br, and Cl) is also attributed to the activation of the C‐2 position through the coordination of nitrogen of quinoline ring with palladium [48, 50, 51].…”
Section: Application Of Cross‐coupling Reactions In the Synthesis Of mentioning
confidence: 99%