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Cho SH, Yoo EJ, Bae I, et al. Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. J Am Chem Soc. 2005;127(46):16046-7doi: 10.1021/ja056399e.
Cho, S. H., Yoo, E. J., Bae, I., & Chang, S. (2005). Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. Journal of the American Chemical Society, 127(46), 16046-7. https://doi.org/10.1021/ja056399e
Cho, Seung Hwan, et al. "Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water." Journal of the American Chemical Society vol. 127,46 (2005): 16046-7. doi: https://doi.org/10.1021/ja056399e
Cho SH, Yoo EJ, Bae I, Chang S. Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. J Am Chem Soc. 2005 Nov 23;127(46):16046-7. doi: 10.1021/ja056399e. PMID: 16287290.
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J Am Chem Soc. 2005 Nov 23;127(46):16046-7. doi: 10.1021/ja056399e.

Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water.

Journal of the American Chemical Society

Seung Hwan Cho, Eun Jeong Yoo, Imhyuck Bae, Sukbok Chang

Affiliations

  1. Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Daejon 305-701, Republic of Korea.

PMID: 16287290 DOI: 10.1021/ja056399e

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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