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Synthesis 1994; 1994(12): 1374-1382
DOI: 10.1055/s-1994-25696
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The Cobalt-Mediated [2+2+2] Cycloaddition of α,ω-Diynes to the 2,3-Double Bond of Indole

Roland Boese* , Andrew P. Van Sickle, K. Peter C. Vollhardt
  • *Institute for Inorganic Chemistry, Universität-Gesamthochschule Essen, Universitätsstraße 5-7, W-4300 Essen 1, FRG
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Publication Date:
25 April 2002 (online)

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The reaction of acetyl or phenylsulfonylindole with α,ω-diynes and CpCo(C2H4)2 yields CpCo-complexed dihydrocarbazoles. 1-Trimethylsilyl-1,6-heptadiyne gives an adduct in which the silyl moiety is distal to the phenylsulfonamide. 1-Trimethylsilyl-1-7-octadiyne results in an unusual diene complex resulting from C-H activation at C-2 of the indole. The behavior of a number of terminally substituted 4-aza-1,7-octadiynes to the reaction is investigated. The oxidation of one dihydrocarbazole complex with triphenylcarbenium hexafluorophosphate or with Fe(NO3)3 furnishes an η5-cyclohexadienyl cobalt complex and its subsequent conversion into substituted diene complexes or to the demetallated carbazole is discussed.