Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions

被引：55

作者：

Ambala, Srinivas ^{[1
,2
]}

Thatikonda, Thanusha ^{[1
,2
]}

Sharma, Shweta ^{[1
]}

Munagala, Gurunadham ^{[1
,2
]}

Yempalla, Kushalava Reddy ^{[1
,2
]}

Vishwakarma, Ram A. ^{[1
,2
]}

Singh, Parvinder Pal ^{[1
,2
]}

机构：

[1] CSIR, Indian Inst Integrat Med, Div Med Chem, Jammu 180001, India

[2] Acad Sci & Innovat Res, Jammu 180001, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 46期

关键词：

ALPHA-OXYALKYLATION; CYCLIC ETHERS; FUNCTIONALIZATION; ESTERIFICATION; QUINOLINES; THIOLATION; RADICALS; ALKANES; BONDS;

D O I：

10.1039/c5ob01268f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we have developed an effective metal-free dehydrogenative coupling method wherein alpha-oxyalkyl and alkyl radicals were generated from various ethers and alkanes to undergo coupling with a variety of electron-deficient heteroarenes such as un/substituted iso-quinolones, quinolines, pyridines, pyrazines and pyrimidines. The persulfate-acetone-water system was optimized for the dehydrogenative coupling with cyclic ethers which gave moderate to excellent yields of alpha-oxyalkyl containing heteroarenes. We have also optimized the conditions for coupling with cyclic alkanes and alicyclic ethers and demonstrated by conducting the reactions with a variety of electron-deficient heteroarenes. Further, the present method is also applicable to electron deficient arenes like naphthoquinones and moreover, it didn't require any external acid.

引用

页码：11341 / 11350

页数：10

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