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Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

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Abstract

An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37 : 63–>99 : 1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.

Graphical abstract: Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

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Publication details

The article was received on 26 Aug 2018, accepted on 12 Sep 2018 and first published on 13 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB02089B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation

    M. Xie, X. Cheng, Y. Chen, X. Wu, G. Qu and H. Guo, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02089B

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