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

Cardiff University

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

64 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

Bibliographical note

Keywords

alcohols
alkylation
borrowing hydrogen
iron catalysis
oxindoles

ASJC Scopus subject areas

Environmental Chemistry
General Chemical Engineering
General Materials Science
General Energy

Access to Document

10.1002/cssc.201900799Licence: CC BY

Cite this

@article{ca3779811dfd433ea8783c0e7540a5c5,

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.\}",

note = "{\textcopyright} 2019 The Authors. Published by Wiley-VCH Verlag GmbH \& Co. KGaA.",

year = "2019",

month = jun,

day = "7",

doi = "10.1002/cssc.201900799",

language = "English",

volume = "12",

pages = "2345--2349",

journal = "ChemSusChem",

issn = "1864-5631",

publisher = "Wiley-VCH Verlag",

number = "11",

}

TY - JOUR

T1 - Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols

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

N2 - 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).

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

UR - https://www.scopus.com/pages/publications/85065487846

U2 - 10.1002/cssc.201900799

DO - 10.1002/cssc.201900799

M3 - Article

C2 - 30958919

AN - SCOPUS:85065487846

SN - 1864-5631

VL - 12

SP - 2345

EP - 2349

JO - ChemSusChem

JF - ChemSusChem

IS - 11

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this