Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles
Publication type: Journal Article
Publication date: 2011-12-09
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
22129424
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.
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240
Total citations:
240
Citations from 2024:
6
(2.5%)
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GOST
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Miura T. et al. Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles // Journal of the American Chemical Society. 2011. Vol. 134. No. 1. pp. 194-196.
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Miura T., Biyajima T., Fujii T., MURAKAMI M. Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles // Journal of the American Chemical Society. 2011. Vol. 134. No. 1. pp. 194-196.
Cite this
RIS
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TY - JOUR
DO - 10.1021/ja2104203
UR - https://doi.org/10.1021/ja2104203
TI - Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles
T2 - Journal of the American Chemical Society
AU - Miura, Tomoya
AU - Biyajima, Tsuneaki
AU - Fujii, Tetsuji
AU - MURAKAMI, MASAHIRO
PY - 2011
DA - 2011/12/09
PB - American Chemical Society (ACS)
SP - 194-196
IS - 1
VL - 134
PMID - 22129424
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2011_Miura,
author = {Tomoya Miura and Tsuneaki Biyajima and Tetsuji Fujii and MASAHIRO MURAKAMI},
title = {Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles},
journal = {Journal of the American Chemical Society},
year = {2011},
volume = {134},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/ja2104203},
number = {1},
pages = {194--196},
doi = {10.1021/ja2104203}
}
Cite this
MLA
Copy
Miura, Tomoya, et al. “Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles.” Journal of the American Chemical Society, vol. 134, no. 1, Dec. 2011, pp. 194-196. https://doi.org/10.1021/ja2104203.