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/atkyl substituted alkynes are used.