A Metal-Free Oxidative Cross-Dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines and 2-Methylazaarenes Using a Recyclable Oxoammonium Salt as Oxidant in Aqueous Media

被引：23
作者：
Fang, Li [1 ]
Li, Zhenhua [1 ,2 ]
Jiang, Zhijiang [2 ]
Tan, Zhiyong [2 ]
Xie, Yuanyuan [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Key Lab Green Pharmaceut Technol & Related Equipm, Minist Educ, Coll Pharmaceut Sci, Chao Wang Rd 18th, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Collaborat Innovat Ctr Yangtze River Delta Reg, Green Pharmaceut, Hangzhou 310014, Zhejiang, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 21期
基金：
中国国家自然科学基金;
关键词：
Cross-coupling; Oxidation; C-C coupling; Green chemistry; SP(3) C-H; BOND FUNCTIONALIZATION; ECTEINASCIDIN; 743; TERTIARY-AMINES; DERIVATIVES; ACID; TETRAFLUOROBORATE; ACTIVATION; INHIBITORS; ALCOHOLS;
D O I：
10.1002/ejoc.201600423
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free oxidative cross-dehydrogenative coupling of N-aryl tetrahydroisoquinolines and 2-methylazaarenes in water under mild conditions has been developed. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate was employed as a mild oxidant that can be recovered and reused directly. The reaction proceeds through formation of an iminium ion in situ followed by condensation with various nucleophiles, providing the desired products in moderate to good yields.
引用
收藏
页码：3559 / 3567
页数：9
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