Tetrahedron letters

Thallium in organic synthesis. 68. A convenient synthesis of 2-phenylindoles from anilides

EC Taylor, AH Katz, H Salgado-Zamora, A McKillop

Index: Taylor, Edward C.; Katz, Alan H.; Salgado-Zamora, Hector Tetrahedron Letters, 1985 ,  vol. 26,  # 48  p. 5963 - 5966

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Citation Number: 98

Abstract

Abstract Thallation of anilides with TTFA in a mixture of TFA and ether gives ortho-thallated derivatives, which yield 2-acetamido-tolanes upon reaction with copper (I) phenylacetylide in acetonitrile. Treatment of the latter compounds with palladium (II) chloride results in ring closure to give 1-acyl-2-phenylindoles, from which 2-phenyl-indoles are obtained by alkaline hydrolysis.