Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes

Wengang Xu; Mingbo Wu; Naohiko Yoshikai

doi:10.1055/a-1337-5416

Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes

Wengang Xu, Mingbo Wu, Naohiko Yoshikai

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

4 Citations (Scopus)

Abstract

An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N -(quinolin-8-yl)benzamides and N -(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.

Original language	English
Pages (from-to)	3144-3150
Number of pages	7
Journal	Synthesis (Germany)
Volume	53
Issue number	17
DOIs	https://doi.org/10.1055/a-1337-5416
Publication status	Published - 2021 Sept 1
Externally published	Yes

Keywords

alkylation
C-H functionalization
iron catalysis
quinolines
radical reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes",

abstract = "An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N -(quinolin-8-yl)benzamides and N -(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.",

keywords = "alkylation, C-H functionalization, iron catalysis, quinolines, radical reaction",

author = "Wengang Xu and Mingbo Wu and Naohiko Yoshikai",

note = "Funding Information: and the China Postdoctoral Science Foundation (Grant No. 31CZ2019010, 05FW2014001 to W.X.).MinisyofEducaton-SingapoeMOE2016-T22043)MinisyofEducaion-SingapoeRG114/18ChinaPotdoctoal ScienceFoundaton31CZ2019010)ChinaPotdocoral ScienceFoundaion(05FW2014001) Funding Information: This work was supported by the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2016-T2-2-043 to N.Y.) and Tier 1 (RG114/18 to N.Y.), the Fundamental Research Funds for China University of Petroleum (China East) (Grant No. 27RA2014007 to W.X.), Publisher Copyright: {\textcopyright} 2021 Georg Thieme Verlag. All rights reserved.",

year = "2021",

month = sep,

day = "1",

doi = "10.1055/a-1337-5416",

language = "English",

volume = "53",

pages = "3144--3150",

journal = "Synthesis",

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publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes

AU - Xu, Wengang

AU - Wu, Mingbo

AU - Yoshikai, Naohiko

N1 - Funding Information: and the China Postdoctoral Science Foundation (Grant No. 31CZ2019010, 05FW2014001 to W.X.).MinisyofEducaton-SingapoeMOE2016-T22043)MinisyofEducaion-SingapoeRG114/18ChinaPotdoctoal ScienceFoundaton31CZ2019010)ChinaPotdocoral ScienceFoundaion(05FW2014001) Funding Information: This work was supported by the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2016-T2-2-043 to N.Y.) and Tier 1 (RG114/18 to N.Y.), the Fundamental Research Funds for China University of Petroleum (China East) (Grant No. 27RA2014007 to W.X.), Publisher Copyright: © 2021 Georg Thieme Verlag. All rights reserved.

PY - 2021/9/1

Y1 - 2021/9/1

N2 - An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N -(quinolin-8-yl)benzamides and N -(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.

AB - An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N -(quinolin-8-yl)benzamides and N -(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.

KW - alkylation

KW - C-H functionalization

KW - iron catalysis

KW - quinolines

KW - radical reaction

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SN - 0039-7881

VL - 53

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JO - Synthesis

JF - Synthesis

IS - 17

ER -

Iron-Catalyzed Remote C-H Alkylation of 8-Amidoquinolines with Cycloalkanes

Abstract

Keywords

ASJC Scopus subject areas

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