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An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride
Abstract
The design and synthesis of a new diazotransfer reagent, imidazole-1-sulfonyl azide hydrochloride, are reported. This reagent has proven to equal triflyl azide in its ability to act as a "diazo donor" in the conversion of both primary amines into azides and activated methylene substrates into diazo compounds. Crucially, this reagent can be prepared in a one-pot reaction on a large scale from inexpensive materials, is shelf-stable, and is conveniently crystalline.
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Cited by
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents
Green, S. P., Wheelhouse, K. M., Payne, A. D., Hallett, J. P., Miller, P. W., & Bull, J. A. (2020) · Organic Process Research & Development · doi:10.1021/acs.oprd.9b00422 · Cited by 363
Modular click chemistry libraries for functional screens using a diazotizing reagent
Meng, G., Guo, T., Ma, T., Zhang, J., Shen, Y., Sharpless, K. B., & Dong, J. (2019) · Nature · doi:10.1038/s41586-019-1589-1 · Cited by 357
Madl, C. M., Katz, L. M., & Heilshorn, S. C. (2016) · Advanced Functional Materials · doi:10.1002/adfm.201505329 · Cited by 156
Metadata
- Authors
- Goddard-Borger, E. D., & Stick, R. V.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-08-22
- Volume
- 9
- Issue
- 19
- Pages
- 3797-3800
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2077498510
- Cited by
- 591
- References
- 0
- FWCI
- 12.16
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride. https://app.cochat.ai/papers/10.1021/ol701581g
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- Goddard-Borger, E. D., & Stick, R. V. (2007). An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride. Organic Letters. https://doi.org/10.1021/ol701581g
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
