Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols

Mubarak B. Dambatta, Kurt Polidano, Alexander D. Northey, Jonathan M.J. Williams, Louis C. Morrill

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A general and efficient iron-catalyzed C-alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono-C3-alkylation in good-to-excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).

Original languageEnglish
Pages (from-to)2345-2349
Number of pages5
JournalChemSusChem
Volume12
Issue number11
Early online date7 May 2019
DOIs
Publication statusPublished - 7 Jun 2019

Keywords

  • alcohols
  • alkylation
  • borrowing hydrogen
  • iron catalysis
  • oxindoles

ASJC Scopus subject areas

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

Cite this

Dambatta, M. B., Polidano, K., Northey, A. D., Williams, J. M. J., & Morrill, L. C. (2019). Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols. ChemSusChem, 12(11), 2345-2349. https://doi.org/10.1002/cssc.201900799