Ni-Catalyzed Reductive Coupling of Alkynes and Amides to Access Multi-Functionalized Indoles
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.
Min, Kwan Hong,Iqbal, Naeem,Cho, Eun Jin
p. 989 - 994
(2022/02/05)
2-Substituted-3-acylindoles through the palladium-catalysed carbonylative cyclization of 2-alkynyltrifluoroacetanilides with aryl halides and vinyl triflates
The palladium-catalysed reaction of readily accessible 2- alkynyltrifluoroacetanilides with aryl halides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) and in the presence of potassium carbonate produces 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.
Arcadi,Cacchi,Carnicelli,Marinelli
p. 437 - 452
(2007/10/02)
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