- Triflic Acid as an Efficient Br?nsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions
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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.).
- Nandi, Raj Kumar,Perez-Luna, Alejandro,Gori, Didier,Beaud, Rodolphe,Guillot, Régis,Kouklovsky, Cyrille,Gandon, Vincent,Vincent, Guillaume
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p. 161 - 172
(2017/11/23)
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- FeCl3-mediated friedel-crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines
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IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl3 features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent. Copyright
- Beaud, Rodolphe,Guillot, Regis,Kouklovsky, Cyrille,Vincent, Guillaume
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supporting information
p. 12546 - 12550
(2013/02/22)
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