One‐Pot Synthesis of Indoles from Aniline and α, β‐Ynones through an Iodine‐Mediated Transition‐Metal‐Free Tandem aza‐Michael addition/C−H Functionalization. Issue 4 (29th March 2019)

• Record Type: Journal Article
• Authors: Su, Jie; Zhang, Kan; Zhuang, Mengyuan; Ma, Fuyu; Zhang, Wei‐Qiang; Sun, Huaming; Zhang, Guofang; Jian, Yajun; Gao, Ziwei
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 4(2019)
• Page Start: 482
• Page End: 486
• Publication Date: 2019-03-29
• Subjects: tandem reactions -- iodine -- C−H activation -- aza-Michael addition -- indoles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900152
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An efficient iodine‐mediated aza ‐Michael addition/C−H functionalization procedure for the synthesis of indoles was achieved in one pot. By simple aza ‐Michael addition between anilines and α, β‐ynones, a series of N ‐aryl enaminones intermediate was generated, followed by iodine‐mediated C−H functionalization, a wide variety of indole derivatives were obtained in moderate to excellent yields under transition‐metal‐free conditions. Control experiments and in situ ESI‐MS analysis indicated the reaction occurred via a radical mechanism. Abstract : Tandem bike : A highly efficient iodine‐mediated aza ‐Michael addition/C−H functionalization procedure for the synthesis of indoles from aniline and α, β‐ynones was achieved. The reaction provides access to a wide variety of indole derivatives, in moderate to excellent yields under transition‐metal‐free conditions.