Oxidative Cross-Coupling of Alcohols and Amines Catalyzed by TEMPO under Transition-Metal-Free Condition

被引：2

作者：

Chandrasekaran, Revathi ^{[1
]}

Carlose, Elgin ^{[1
]}

Muthu, Ajun E. ^{[1
]}

Suresh, Athira ^{[1
]}

Chinnusamy, Tamilselvi ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Thiruvananthapuram, Sch Chem, Thiruvananthapuram 695551, Kerala, India

来源：

CHEMISTRYSELECT | 2020年 / 5卷 / 21期

关键词：

Cross-Coupling; Imines; Nitrogen heterocycles; TEMPO; Thiabutazide; ONE-POT SYNTHESIS; AEROBIC OXIDATION; SECONDARY-AMINES; 2-SUBSTITUTED QUINAZOLINES; MICHAEL-ADDITION; N-ALKYLATION; IMINES; EFFICIENT; RUTHENIUM; ALDEHYDES;

D O I：

10.1002/slct.202001417

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The transition-metal-free catalytic system TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl)/NaOCl promotes an efficient oxidative cross-coupling of alcohols and amines to imines4as well as 1,2,3,4-tetrahydroquniazolines6. A wide variety of alcohols and amines were well tolerated in the catalytic condition. This protocol was operationally very simple, efficiently scaled up to 100 mmol with as low as 0.5 mol% of catalyst loading and applied to the synthesis of biologically important diuretic drug molecule thiabutazide9in 98% yield. The recyclable TEMPO catalyst was showed similar reactivity. Moreover, it was reused upto five runs without much drop in the activity. The green chemistry metrics of the estabilished method (E-factor value 17.80, Atom economy 90.7%, Carbon efficiency 98% and Overall efficiency 97.95%) proved to be efficient to the existing methods.

引用

页码：6285 / 6293

页数：9

共 78 条

[1] Imines, enamines and oximes [J].