Tetrahedron p. 3775 - 3780 (2016)
Update date:2022-08-16
Topics:
Lofstrand, Verner A.
Matsuura, Bryan S.
Furst, Laura
Narayanam, Jagan M.R.
Stephenson, Corey R.J.
The one-pot, three-component, coupling reaction of indoles/pyrroles, dimethyl malonate, and acetic acid was performed using Mn(III) acetate as an oxidant. In the presence of Mn(OAc)3, indole-2, and indole-3-carbonyl compounds were alkylated at the 3- and 2- positions, respectively, with subsequent oxidation and nucleophilic capture occurring at the newly formed benzylic carbon. In contrast, oxidation of 2- and 3-indole carboxylic acids afforded the corresponding 2-oxindol-3-ylidenes and 3-oxindol-2-ylidenes. The reaction conditions, scope, and mechanism are discussed herein.
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