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Silver Acetate Catalyzed Hydroamination of 1‑(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2‑Methylene-1-sulfonylindolin-3-ols

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journal contribution
posted on 07.09.2012, 00:00 by Dewi Susanti, Fujiet Koh, Jeffrey Antonius Kusuma, Prasath Kothandaraman, Philip Wai Hong Chan
A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)­phenyl)­prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.