C(sp3)–H Azidation Reaction: A Protocol for Preparation of Aminals

We report a protocol for the synthesis of N,N- and N,O-aminals via direct azidation of sp3 C–H bonds of substrates with an α-nitrogen or α-oxygen atom. A broad range of tetrahydroisoquinolines, tetrahydro-β-carbolines, and cyclic benzyl ethers gave high yields under mild conditions. The protocol cou...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-04, Vol.83 (8), p.4516-4524
Main Authors: Dong, Jianyang, Xia, Qing, Yan, Changcun, Song, Hongjian, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
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Summary:We report a protocol for the synthesis of N,N- and N,O-aminals via direct azidation of sp3 C–H bonds of substrates with an α-nitrogen or α-oxygen atom. A broad range of tetrahydroisoquinolines, tetrahydro-β-carbolines, and cyclic benzyl ethers gave high yields under mild conditions. The protocol could be carried out on a gram scale without a decrease in the yield, and the aminal products could be readily transformed into complex aminals.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00235