Indole synthesis via rhodium catalyzed oxidative coupling of acetanilides and internal alkynes.

By David R. Stuart, Mégan Bertrand-Laperle, K. Burgess, K. Fagnou. Journal of the American Chemical Society, 2008

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The oxidative synthesis of highly functionalized indoles from simple anilines and internal alkynes mediated by a rhodium(III) catalyst is described. Good yields are obtained for a variety of aniline substrates, and good regioselectivity is obtained for the more sterically accessible position when meta-substituted anilines are used. Symmetrical and unsymmetrical alkynes react efficiently with high (>40:1) C2/C3 regioselectivity when aryl/alkyl substituted alkynes are used.

Subfields: Organic Chemistry

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