Copper-Catalyzed Remote C5-Selective Chlorination of 8-Amidoquinolines Using Sulfonyl Chlorides as Cl Source

Han Zhang; Miao Xu; Ningning Liu; Fanzhi Yang

doi:10.1002/slct.202100030

Copper-Catalyzed Remote C5-Selective Chlorination of 8-Amidoquinolines Using Sulfonyl Chlorides as Cl Source

Han Zhang
, Miao Xu
, Ningning Liu
, Fanzhi Yang^*

^*Corresponding author for this work

Advanced Research Institute of Multidisciplinary Science

Beijing Institute of Technology

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

6 Citations (Scopus)

Abstract

Sulfonyl chloride has been rarely used as Cl source in transition metal-catalyzed C−H functionalizations. We report the unprecedented copper-catalyzed remote C5-chlorination of substituted 8-amidoquinolines with sulfonyl chloride under 1 atm oxygen. 10 sulfonyl chlorides and 15 substituted 8-amidoquinolines were tested, generating moderate to high yields. The catalytic system showed high regio-selectivity, as well as good functional group tolerance.

Original language	English
Pages (from-to)	2319-2322
Number of pages	4
Journal	ChemistrySelect
Volume	6
Issue number	9
DOIs	https://doi.org/10.1002/slct.202100030
Publication status	Published - 5 Mar 2021

Keywords

chlorination
copper catalysis
quinoline
remote selectivity
sulfonyl chloride

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10.1002/slct.202100030

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title = "Copper-Catalyzed Remote C5-Selective Chlorination of 8-Amidoquinolines Using Sulfonyl Chlorides as Cl Source",

abstract = "Sulfonyl chloride has been rarely used as Cl source in transition metal-catalyzed C−H functionalizations. We report the unprecedented copper-catalyzed remote C5-chlorination of substituted 8-amidoquinolines with sulfonyl chloride under 1 atm oxygen. 10 sulfonyl chlorides and 15 substituted 8-amidoquinolines were tested, generating moderate to high yields. The catalytic system showed high regio-selectivity, as well as good functional group tolerance.",

keywords = "chlorination, copper catalysis, quinoline, remote selectivity, sulfonyl chloride",

author = "Han Zhang and Miao Xu and Ningning Liu and Fanzhi Yang",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

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T1 - Copper-Catalyzed Remote C5-Selective Chlorination of 8-Amidoquinolines Using Sulfonyl Chlorides as Cl Source

AU - Zhang, Han

AU - Xu, Miao

AU - Liu, Ningning

AU - Yang, Fanzhi

PY - 2021/3/5

Y1 - 2021/3/5

N2 - Sulfonyl chloride has been rarely used as Cl source in transition metal-catalyzed C−H functionalizations. We report the unprecedented copper-catalyzed remote C5-chlorination of substituted 8-amidoquinolines with sulfonyl chloride under 1 atm oxygen. 10 sulfonyl chlorides and 15 substituted 8-amidoquinolines were tested, generating moderate to high yields. The catalytic system showed high regio-selectivity, as well as good functional group tolerance.

AB - Sulfonyl chloride has been rarely used as Cl source in transition metal-catalyzed C−H functionalizations. We report the unprecedented copper-catalyzed remote C5-chlorination of substituted 8-amidoquinolines with sulfonyl chloride under 1 atm oxygen. 10 sulfonyl chlorides and 15 substituted 8-amidoquinolines were tested, generating moderate to high yields. The catalytic system showed high regio-selectivity, as well as good functional group tolerance.

KW - chlorination

KW - copper catalysis

KW - quinoline

KW - remote selectivity

KW - sulfonyl chloride

UR - https://www.scopus.com/pages/publications/85102068136

U2 - 10.1002/slct.202100030

DO - 10.1002/slct.202100030

M3 - Article

AN - SCOPUS:85102068136

SN - 2365-6549

VL - 6

SP - 2319

EP - 2322

JO - ChemistrySelect

JF - ChemistrySelect

IS - 9

ER -

Copper-Catalyzed Remote C5-Selective Chlorination of 8-Amidoquinolines Using Sulfonyl Chlorides as Cl Source

Abstract

Keywords

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