Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position

Longzhi Zhu; Renhua Qiu; Xin Cao; Song Xiao; Xinhua Xu; Chak Tong Au; Shuang Feng Yin

doi:10.1021/acs.orglett.5b02511

Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position

Longzhi Zhu
, Renhua Qiu^*
, Xin Cao
, Song Xiao
, Xinhua Xu
, Chak Tong Au
, Shuang Feng Yin^*

^*Corresponding author for this work

Department of Chemistry

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

142 Citations (Scopus)

Abstract

An efficient and convenient method is developed for the remote C-H bond chalcogenation of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. The protocol makes use of inexpensive CuBr₂ as mediator and shows good tolerance toward numerous disulfides/diselenides and aliphatic amides, giving the corresponding products in good to excellent yield.

Original language	English
Pages (from-to)	5528-5531
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.5b02511
Publication status	Published - 20 Nov 2015

Access to Document

10.1021/acs.orglett.5b02511

Cite this

@article{3c206ebe3e9442648110c3c665f10b4c,

title = "Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position",

abstract = "An efficient and convenient method is developed for the remote C-H bond chalcogenation of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. The protocol makes use of inexpensive CuBr2 as mediator and shows good tolerance toward numerous disulfides/diselenides and aliphatic amides, giving the corresponding products in good to excellent yield.",

author = "Longzhi Zhu and Renhua Qiu and Xin Cao and Song Xiao and Xinhua Xu and Au, \{Chak Tong\} and Yin, \{Shuang Feng\}",

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

year = "2015",

month = nov,

day = "20",

doi = "10.1021/acs.orglett.5b02511",

language = "English",

volume = "17",

pages = "5528--5531",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position

AU - Zhu, Longzhi

AU - Qiu, Renhua

AU - Cao, Xin

AU - Xiao, Song

AU - Xu, Xinhua

AU - Au, Chak Tong

AU - Yin, Shuang Feng

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

PY - 2015/11/20

Y1 - 2015/11/20

N2 - An efficient and convenient method is developed for the remote C-H bond chalcogenation of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. The protocol makes use of inexpensive CuBr2 as mediator and shows good tolerance toward numerous disulfides/diselenides and aliphatic amides, giving the corresponding products in good to excellent yield.

AB - An efficient and convenient method is developed for the remote C-H bond chalcogenation of 8-aminoquinoline scaffolds on the C5 position that is geometrically inaccessible. The protocol makes use of inexpensive CuBr2 as mediator and shows good tolerance toward numerous disulfides/diselenides and aliphatic amides, giving the corresponding products in good to excellent yield.

UR - https://www.scopus.com/pages/publications/84947968741

U2 - 10.1021/acs.orglett.5b02511

DO - 10.1021/acs.orglett.5b02511

M3 - Journal article

AN - SCOPUS:84947968741

SN - 1523-7060

VL - 17

SP - 5528

EP - 5531

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Copper-Mediated Remote C-H Bond Chalcogenation of Quinolines on the C5 Position

Abstract

Access to Document

Other files and links

Fingerprint

Cite this