Copper‐Catalyzed Remote C5‐Selective Chlorination of 8‐Amidoquinolines Using Sulfonyl Chlorides as Cl Source. Issue 9 (2nd March 2021)

• Record Type: Journal Article
• Authors: Zhang, Han; Xu, Miao; Liu, Ningning; Yang, Fanzhi
• Is Part Of: ChemistrySelect. Volume 6:Issue 9(2021)
• Page Start: 2319
• Page End: 2322
• Publication Date: 2021-03-02
• Subjects: remote selectivity -- copper catalysis -- sulfonyl chloride -- quinoline -- chlorination; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202100030
• Languages: English
• ISSNs: 2365-6549

Abstract

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. Abstract : A new method of copper‐catalyzed remote C5‐functionalization of 8‐amidoquinolines using sulfonyl chlorides, instead of forming C−H sulfonated quinoline, the C5‐chorinated 8‐amidoquinolines was isolated as the sole product. This system showed high regio‐selectivity, good catalytic activity, and good functional group tolerance. A SET pathway is proposed in the catalytic cycle.