1640122-66-2Relevant academic research and scientific papers
Triflic Acid as an Efficient Br?nsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions
Nandi, Raj Kumar,Perez-Luna, Alejandro,Gori, Didier,Beaud, Rodolphe,Guillot, Régis,Kouklovsky, Cyrille,Gandon, Vincent,Vincent, Guillaume
, p. 161 - 172 (2017/11/23)
We report that triflic acid, a strong Br?nsted acid, is a very powerful alternative to FeCl3 to mediate the hydroarylation of N?Ac indoles, which delivers regioselectively 3-arylindolines, 3,3-spiroindolines or 2-arylindolines. Mechanistic explorations point towards the existence of a highly electrophilic intermediate by simultaneous activation of the acetyl and of the C2=C3 bond by protons. (Figure presented.).
Regioselective hydroarylation reactions of C3 electrophilic N-acetylindoles activated by FeCl3: An entry to 3-(Hetero)arylindolines
Beaud, Rodolphe,Guillot, Regis,Kouklovsky, Cyrille,Vincent, Guillaume
supporting information, p. 7492 - 7500 (2014/06/23)
A method for the direct and rare umpolung of the 3 position of indoles is reported. The activation of N-acetylindole with iron(III) chloride allows the C-H addition of aromatic and heteroaromatic substrates to the C2-C3 double bond of the indole nucleus to generate a quaternary center at C3 and leads regioselectively to 3-arylindolines. Optimization, scope (50 examples), practicability (gram scale, air atmosphere, room temperature), and mechanistic insights of this process are presented. Synthetic transformations of the indoline products into drug-like compounds are also described.
