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Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole

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Abstract

BF3·Et2O promoted metal-free denitrogenative transannulation of N-sulfonyl-1,2,3-triazole was reported. Rather than transition metals, BF3·Et2O was employed for the first time to promote the formation of α-diazoimines from N-sulfonyl-1,2,3-triazoles in nitriles, leading to the synthesis of various imidazoles. The protocol tolerates a broad range of functional groups and could also be applied to the late-stage modification of bioactive molecules, demonstrating the potential of this protocol in organic synthesis. A plausible mechanism was proposed.

Graphical abstract: Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole

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Publication details

The article was received on 11 Jan 2018, accepted on 07 Feb 2018 and first published on 07 Feb 2018


Article type: Communication
DOI: 10.1039/C8OB00083B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole

    D. Yang, L. Shan, Z. Xu and C. Li, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB00083B

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