2018
DOI: 10.1055/s-0037-1609558
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Palladium-Catalyzed Arylation of Aromatic Amides Directed by a [4-Chloro-2-(1H-pyrazol-1-yl)phenyl]amine Auxiliary

Abstract: A palladium-catalyzed ortho-arylation of aromatic amides ­directed by [4-chloro-2-(1H-pyrazol-1-yl)phenyl]amine as a bidentate auxiliary has been established. The reaction is characterized by normal working conditions, a broad substrate scope, and a wide functional-group tolerance. In particular, the protocol is compatible with highly sterically demanding ortho-substituted anilides and aryl iodide partners, with good yields.

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Cited by 9 publications
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“…In particular, the ortho -methoxy-substituted oxime ether gave a reduced yield of 56% ( 3n ). It is possibly because of potentially strong chelation of the methoxy with the catalyst, leading to the blocked catalytic cycle . Furthermore, the fused-cyclic substrates were also reacted smoothly to produce 3q–3r in lower yields albeit with prolonged reaction time.…”
Section: Resultsmentioning
confidence: 99%
“…In particular, the ortho -methoxy-substituted oxime ether gave a reduced yield of 56% ( 3n ). It is possibly because of potentially strong chelation of the methoxy with the catalyst, leading to the blocked catalytic cycle . Furthermore, the fused-cyclic substrates were also reacted smoothly to produce 3q–3r in lower yields albeit with prolonged reaction time.…”
Section: Resultsmentioning
confidence: 99%