Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
Sandrine M Hell
1
,
Claudio F Meyer
1, 2
,
Antonio Misale
2
,
M. J. Willis
1
,
Timothy R. Noel
3
,
Andrés Avelino Trabanco
2
,
2
Discovery Chemistry, Janssen Research and Development, Jarama 75A, Toledo E-45007, Spain
|
Publication type: Journal Article
Publication date: 2019-12-27
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
31881153
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
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112
Total citations:
112
Citations from 2024:
42
(37.5%)
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MLA
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GOST
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Hell S. M. et al. Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes // Journal of the American Chemical Society. 2019. Vol. 142. No. 2. pp. 720-725.
GOST all authors (up to 50)
Copy
Hell S. M., Meyer C. F., Laudadio G., Misale A., Willis M. J., Noel T. R., Trabanco A. A., Gouverneur V. Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes // Journal of the American Chemical Society. 2019. Vol. 142. No. 2. pp. 720-725.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jacs.9b13071
UR - https://doi.org/10.1021/jacs.9b13071
TI - Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
T2 - Journal of the American Chemical Society
AU - Hell, Sandrine M
AU - Meyer, Claudio F
AU - Laudadio, Gabriele
AU - Misale, Antonio
AU - Willis, M. J.
AU - Noel, Timothy R.
AU - Trabanco, Andrés Avelino
AU - Gouverneur, Véronique
PY - 2019
DA - 2019/12/27
PB - American Chemical Society (ACS)
SP - 720-725
IS - 2
VL - 142
PMID - 31881153
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Hell,
author = {Sandrine M Hell and Claudio F Meyer and Gabriele Laudadio and Antonio Misale and M. J. Willis and Timothy R. Noel and Andrés Avelino Trabanco and Véronique Gouverneur},
title = {Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes},
journal = {Journal of the American Chemical Society},
year = {2019},
volume = {142},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jacs.9b13071},
number = {2},
pages = {720--725},
doi = {10.1021/jacs.9b13071}
}
Cite this
MLA
Copy
Hell, Sandrine M., et al. “Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes.” Journal of the American Chemical Society, vol. 142, no. 2, Dec. 2019, pp. 720-725. https://doi.org/10.1021/jacs.9b13071.
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