Redox Chain Reaction—Indole and Pyrrole Alkylation with Unactivated Secondary Alcohols


  • J.W. acknowledges financial support provided by Dartmouth College. We thank Dr. Richard J. Staples (Michigan State University, USA) for assistance with X-ray crystallography. We also thank Lotus Separations (Princeton, NJ, USA) for their generous donation of analytical work.


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Secondary role: Indole and pyrrole derivatives are alkylated with unactivated secondary aliphatic alcohols by a Brønsted acid-catalyzed redox chain reaction mechanism. Broad functional-group tolerance has been demonstrated and preliminary studies suggest that 1,4-reduction of a putative indolyl carbocation is the dominant mechanistic pathway.