Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group. Issue 1 (14th November 2019)

• Record Type: Journal Article
• Authors: Yu, Shuling; Lv, Ningning; Liu, Zhanxiang; Zhang, Yuhong
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 1(2020)
• Page Start: 118
• Page End: 125
• Publication Date: 2019-11-14
• Subjects: traceless directing group -- C−H activation -- cascade reaction -- benzofurans synthesis -- chemoselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901316
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A copper‐mediated synthesis of 2, 3‐disubstituted benzofurans with the assistance of an 8‐aminoquinolyl auxiliary is described from readily available benzamides and benzoylacetonitriles. In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached simultaneously under the reaction conditions through C−C bond cleavage. Surprisngly, the distinct isoquinolinone products can be achieved by changing the reaction conditions using ammonia as amine source. Abstract :