Cross-dehydrogenative coupling of α-C(sp(3))-H of ethers/alkanes with C(sp(2))-H of heteroarenes under metal-free conditions

Here we have developed an effective metal-free dehydrogenative coupling method wherein α-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, pyra...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-12, Vol.13 (46), p.11341-11350
Main Authors: Ambala, Srinivas, Thatikonda, Thanusha, Sharma, Shweta, Munagala, Gurunadham, Yempalla, Kushalava Reddy, Vishwakarma, Ram A, Singh, Parvinder Pal
Format: Article
Language:English
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Summary:Here we have developed an effective metal-free dehydrogenative coupling method wherein α-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 α-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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01268f