The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
Copper-Catalyzed Hydrative Amide Synthesis with Terminal Alkyne, Sulfonyl Azide, and Water
Abstract
It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions. The present route is quite general, and a wide range of alkynes and sulfonyl azides are readily coupled catalytically with water to furnish amides in high yields. A variety of labile functional groups are tolerated under the conditions, and the reaction is regioselective in that only terminal alkynes react while double or internal triple bonds are intact. The reaction can be readily scaled up and is also adaptable to a solid-phase procedure with high efficiency.
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Cites
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Staudinger Ligation: A Peptide from a Thioester and Azide
Nilsson, B. L., Kiessling, L. L., & Raines, R. T. (2000) · Organic Letters · doi:10.1021/ol0060174 · Cited by 533
Bae, I., Han, H., & Chang, S. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0432968 · Cited by 479
Self-citationRecent advances in the chemistry of ynamines and ynamides
Zificsak, C. A., Mulder, J. A., Hsung, R. P., Rameshkumar, C., & Wei, L.-L. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00681-0 · Cited by 303
Developments in peptide and amide synthesis
Albericio, F. (2004) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2004.03.002 · Cited by 257
Merkx, R., Brouwer, A. J., Rijkers, D. T. S., & Liskamp, R. M. J. (2005) · Organic Letters · doi:10.1021/ol0501119 · Cited by 92
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Cited by
Amblard, F., Cho, J. H., & Schinazi, R. F. (2009) · Chemical Reviews · doi:10.1021/cr9001462 · Cited by 802
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
Chemoselectivity and the Curious Reactivity Preferences of Functional Groups
Afagh, N. A., & Yudin, A. K. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200901317 · Cited by 320
Umpolung reactivity in amide and peptide synthesis
Shen, B., Makley, D. M., & Johnston, J. N. (2010) · Nature · doi:10.1038/nature09125 · Cited by 318
Metadata
- Authors
- Cho, S. H., Yoo, E. J., Bae, I., & Chang, S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-11-01
- Volume
- 127
- Issue
- 46
- Pages
- 16046-16047
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2039766994
- Cited by
- 447
- References
- 12
- FWCI
- 9.33
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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