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Paper | Special issue | Vol 50, No. 2, 1999, pp.875-885
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)84
Preparation of 4-Iodo-β-carboline-3-carboxamide via ortho-Metalation and Its Use in Palladium-catalyzed Carbon-Carbon Bond Forming Reactions with Unsaturated Substrates

Alexandre Batch and Robert H. Dodd*

*Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


The 4-iodo derivative of N-9 protected β-carboline-3-(N-methyl)-3-(N-phenyl)carboxamide (12) was prepared by sequential treatment of N-9 protected β-carboline-3-(N-phenyl)carboxamide (2) with methyllithium, iodine and methyl iodide. Compound (12), in the presence of catalytic palladium acetate and tri-o-tolylphosphine in acetonitrile and triethylamine, reacted with a variety of unsaturated substrates (styrenes, acrylate, tributyl(vinyl)tin, trimethylsilylacetylene) to give the corresponding C-4 coupled adducts (13a-g).