Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: an aryne twist of Bischler-Möhlau indole synthesis.
Reaction of 2-(trimethylsilyl)aryl triflates 1 with N-aryl-α-amino ketones 2 afforded N-aryl-2,3-disubstituted indoles in good to excellent yields with complete control of the substitution patterns. This methodology allowed for the first time a one-step synthesis of unsymmetrical 2,3-dialkyl substituted indoles in a regiospecific manner.
Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland. jieping.zhu@epfl.ch.
Ala
A
Bunescu
Cyril
C
Piemontesi
Qian
Q
Wang
Jieping
J
Zhu
D001190:Arylsulfonates / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure
D001190:Arylsulfonates; D007211:Indoles; D007659:Ketones