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

doi:10.1002/cssc.201900799

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

44 Citations (SciVal)

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 language	English
Pages (from-to)	2345-2349
Number of pages	5
Journal	ChemSusChem
Volume	12
Issue number	11
Early online date	7 May 2019
DOIs	https://doi.org/10.1002/cssc.201900799
Publication status	Published - 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)

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10.1002/cssc.201900799Licence: CC BY

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title = "Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols",

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).",

keywords = "alcohols, alkylation, borrowing hydrogen, iron catalysis, oxindoles",

author = "Dambatta, {Mubarak B.} and Kurt Polidano and Northey, {Alexander D.} and Williams, {Jonathan M.J.} and Morrill, {Louis C.}",

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AU - Dambatta, Mubarak B.

AU - Polidano, Kurt

AU - Northey, Alexander D.

AU - Williams, Jonathan M.J.

AU - Morrill, Louis C.

PY - 2019/6/7

Y1 - 2019/6/7

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AB - 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).

KW - alcohols

KW - alkylation

KW - borrowing hydrogen

KW - iron catalysis

KW - oxindoles

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JO - ChemSusChem

JF - ChemSusChem

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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