Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes

Xie Wang; Longzhi Zhu; Sihai Chen; Xinhua Xu; Chak Tong Au; Renhua Qiu

doi:10.1021/acs.orglett.5b02572

Nickel-Catalyzed Direct C (sp³)-H Arylation of Aliphatic Amides with Thiophenes

Xie Wang
, Longzhi Zhu
, Sihai Chen
, Xinhua Xu^*
, Chak Tong Au
, Renhua Qiu^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

43 Citations (Scopus)

Abstract

Nickel-catalyzed heteroarylation of the inactive methyl C(sp³)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.

Original language	English
Pages (from-to)	5228-5231
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.5b02572
Publication status	Published - 6 Nov 2015

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10.1021/acs.orglett.5b02572

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title = "Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes",

abstract = "Nickel-catalyzed heteroarylation of the inactive methyl C(sp3)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.",

author = "Xie Wang and Longzhi Zhu and Sihai Chen and Xinhua Xu and Au, \{Chak Tong\} and Renhua Qiu",

note = "Funding information: We thank the NSFC (Nos. 21373003, 21273068, J1210040) and the Fundamental Research Funds for the Central Universities for financial support. R.Q. thanks Prof. Nobuaki Kambe (Osaka University, Japan), Prof. Akihiro Orita (Okayama University of Science, Japan), and Prof. Li-Biao Han (AIST, Tsukuba, Japan) for helpful discussions. C.-T.A. thanks HNU for an adjunct professorship. Publisher copyright: {\textcopyright} 2015 American Chemical Society",

year = "2015",

month = nov,

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doi = "10.1021/acs.orglett.5b02572",

language = "English",

volume = "17",

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journal = "Organic Letters",

issn = "1523-7060",

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T1 - Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes

AU - Wang, Xie

AU - Zhu, Longzhi

AU - Chen, Sihai

AU - Xu, Xinhua

AU - Au, Chak Tong

AU - Qiu, Renhua

N1 - Funding information: We thank the NSFC (Nos. 21373003, 21273068, J1210040) and the Fundamental Research Funds for the Central Universities for financial support. R.Q. thanks Prof. Nobuaki Kambe (Osaka University, Japan), Prof. Akihiro Orita (Okayama University of Science, Japan), and Prof. Li-Biao Han (AIST, Tsukuba, Japan) for helpful discussions. C.-T.A. thanks HNU for an adjunct professorship. Publisher copyright: © 2015 American Chemical Society

PY - 2015/11/6

Y1 - 2015/11/6

N2 - Nickel-catalyzed heteroarylation of the inactive methyl C(sp3)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.

AB - Nickel-catalyzed heteroarylation of the inactive methyl C(sp3)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.

UR - https://www.scopus.com/pages/publications/84946748454

U2 - 10.1021/acs.orglett.5b02572

DO - 10.1021/acs.orglett.5b02572

M3 - Journal article

AN - SCOPUS:84946748454

SN - 1523-7060

VL - 17

SP - 5228

EP - 5231

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Nickel-Catalyzed Direct C (sp³)-H Arylation of Aliphatic Amides with Thiophenes

Abstract

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