Diamination/Oxidative Cross-Coupling/Bicyclization of Anilines and Methyl Ketones: Direct I2-Promoted Synthesis of 1,2-Fused Oxindoles

详细信息    查看全文

• 作者：Jingjing Zhang ; Xia Wu ; Qinghe Gao ; Xiao Geng ; Peng Zhao ; Yan-Dong Wu ; Anxin Wu
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：19
• 期：2
• 页码：408-411
• 全文大小：377K
• ISSN：1523-7052

文摘

An I₂-promoted domino bicyclization approach via multiple sequential C–H functionalization was serendipitously discovered for the synthesis of 1,2-fused oxindoles from methyl ketones and anilines. This approach was optimized, resulting in a concise and atom-economical approach for the one-pot construction of 1,2-fused oxindoles from methyl ketones and anilines rather than using preexisting indolin-3-ones or indoles. Mechanistic studies revealed that the key step involved an oxidative cross-coupling between in situ generated phenylglyoxal and α,α-diaminoketone.