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Ni-Catalyzed Reductive Coupling of Alkynes and Amides to Access Multi-Functionalized Indoles.

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A nickel-catalyzed reductive coupling of alkynes and amides, followed by base-free transmetalation, proceeded selectively in the presence of an uncommon bidentate primary aminophosphine ligand to access highly functionalized indoles comprising… Click to show full abstract

A nickel-catalyzed reductive coupling of alkynes and amides, followed by base-free transmetalation, proceeded selectively in the presence of an uncommon bidentate primary aminophosphine ligand to access highly functionalized indoles comprising biologically important trifluoromethyl groups and challenging electron-rich alkenyl groups at the 2- and 3-positions, respectively. Indole molecules were installed within natural products or drug molecules under mild conditions, and a trifluoromethylated analogue of a drug molecule (pravadoline) was also synthesized.

Keywords: functionalized indoles; alkynes amides; reductive coupling; catalyzed reductive; coupling alkynes

Journal Title: Organic letters
Year Published: 2022

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