New substitution reactions on indole promoted by the Cr(CO)3 unit

Martin F. Semmelhack, W. Wulff, J. L. Garcia

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Abstract

Indole derivatives form complexes with the Cr(CO)3 unit at the 6-membered ring. Addition of reactive carbon nucleophiles occurs at the coordinated ring with strong preference for C-4 and, in a few cases, for C-7. Oxidation of the intermediate cyclohexadienyl anionic complexes produces substituted indoles in good yield. Complexes of N-methylindoline and benzofuran also undergo the addition/oxidation sequence preferentially at C-4. Changes in the substituents at C-3 and the nitrogen atom in the indole complexes influences the regioselectivity so that either C-4 or C-7 substitution can be observed. The selectivity is correlated with EHT calculations on free indole and complexes indole.

Original languageEnglish (US)
JournalJournal of Organometallic Chemistry
Volume240
Issue number1
DOIs
StatePublished - Dec 7 1982

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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