Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates

Palladium-catalysed reactions of aryl iodides/vinyl triflates with 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]buta-1,3-diynyl)-phenyl)-acetamide provide a straightforward entry into 3,3'-disubstituted-2,2'-biindolyls. Subsequent application of the procedure to homochiral aryl iodides affords the corresponding chiral 3,3'-disubstituted-2,2'-biindolyls. The methodology can also be applied to the synthesis of benzo[c]indolo[2,3-a]carbazoles. (c) 2006 Elsevier Ltd. All rights reserved.