I2-Triggered Reductive Generation of N-Centered Iminyl Radicals: An Isatin-to-Quinoline Strategy for the Introduction of Primary Amides

被引：47
作者：
Gao, Qinghe [1 ]
Liu, Zhaomin [1 ]
Wang, Yakun [1 ]
Wu, Xia [2 ]
Zhang, Jixia [1 ]
Wu, Anxin [2 ]
机构：
[1] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China
[2] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 07期
基金：
中国国家自然科学基金;
关键词：
Amidation; organocatalysis; iminyl radicals; drug design; PALLADIUM-CATALYZED AMINOCARBONYLATION; AROMATIC PRIMARY AMIDES; C-H FUNCTIONALIZATION; METAL-FREE CONDITIONS; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; METHYL KETONES; BOND FORMATION; DIRECT TRANSFORMATION; OXIDATIVE AMIDATION;
D O I：
10.1002/adsc.201701610
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient and alternative isatin-to-quinoline strategy illustrates the metal-like behavior of molecular iodine in the N-O reduction of ketoxime acetates. This process involves N-O/C-N bond cleavages and C-C/C-N bond formation to furnish pharmacologically significant quinoline-4-carboxamide derivatives. In this process, metal catalysts and extra oxidants are unnecessary. Mechanistic studies confirm the crucial role of molecular iodine in the iminyl radical generation process, in that molecular iodine can catalyze single-electron reduction coupling reactions in a manner similar to transition metals.
引用
收藏
页码：1364 / 1369
页数：6
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