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

4 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

Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols. / Dambatta, Mubarak B.; Polidano, Kurt; Northey, Alexander D.; Williams, Jonathan M.J.; Morrill, Louis C.

In: ChemSusChem, Vol. 12, No. 11, 07.06.2019, p. 2345-2349.

Research output: Contribution to journalArticle

Dambatta, MB, Polidano, K, Northey, AD, Williams, JMJ & Morrill, LC 2019, 'Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols', ChemSusChem, vol. 12, no. 11, pp. 2345-2349. https://doi.org/10.1002/cssc.201900799
Dambatta MB, Polidano K, Northey AD, Williams JMJ, Morrill LC. Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols. ChemSusChem. 2019 Jun 7;12(11):2345-2349. https://doi.org/10.1002/cssc.201900799
Dambatta, Mubarak B. ; Polidano, Kurt ; Northey, Alexander D. ; Williams, Jonathan M.J. ; Morrill, Louis C. / Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols. In: ChemSusChem. 2019 ; Vol. 12, No. 11. pp. 2345-2349.
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