Synthesis of 2,2'-biindolyls by coupling reactions |
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Authors: | Jan Bergman Nils Eklund |
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Institution: | Department of Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden |
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Abstract: | Coupling reactions of indoles forming 2,2'-biindolyls have been investigated. 2-Iodo-N-methyl-indole and unactivated copper gave N,N'-dimethyl-2,2'-biindolyl whereas activated copper yielded N-methyl-indole and the symmetrical trisindolobenzene 5. A mechanism involving the elimination of copper hydride to form a hetaryne intermediate is suggested.Coupling of N-benzenesulfonyl-2-lithioindole with CuCl2 yielded 2,2'-biindolyl after hydrolysis. N-methyl-2-lithioindole likewise gave N,N'-dimethyl-2,2'-biindolyl. |
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