Oxidative sulfonamidation of O-containing vinylsilanes. A new route to novel heterocycles and amidines
Publication type: Journal Article
Publication date: 2021-10-01
scimago Q3
wos Q2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
• Oxidative amination of unsaturated Si–O-containing compounds with various sulfonamides is studied. • The reaction course strongly depends on the structure of the substrate, the NH acidity of sulfonamide and on the oxidant. • Novel products of halosulfonamidation, heterocyclization, halogenation, solvent interception and desilylation are obtained. • Tentative mechanisms are proposed to explain the formation of numerous unexpected products. The reactions of sulfonamidation of 1,1,3,3-tetramethyl-1,3-divinyldisiloxane, (allyloxy)trimethylsilane, trimethoxy(vinyl)silane and tris(2-methoxyethoxy)vinylsilane with trifluoromethanesulfonamide, arenesulfonamides and methanesulfonamide in the presence of ( t -BuOCl + NaI) or N-bromosuccinimide proceed in a different manner depending on the substrate, reagent, and oxidant. The formation of the products of halosulfonamidation, heterocyclization, halogenation, solvent interception and desilylation is observed.
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Moskalik M. Yu. et al. Oxidative sulfonamidation of O-containing vinylsilanes. A new route to novel heterocycles and amidines // Journal of Organometallic Chemistry. 2021. Vol. 951. p. 122010.
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Moskalik M. Yu., Garagan I. A., Ganin A. S., Astakhova V. V., Sterkhova I., Shainyan B. A. Oxidative sulfonamidation of O-containing vinylsilanes. A new route to novel heterocycles and amidines // Journal of Organometallic Chemistry. 2021. Vol. 951. p. 122010.
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TY - JOUR
DO - 10.1016/j.jorganchem.2021.122010
UR - https://doi.org/10.1016/j.jorganchem.2021.122010
TI - Oxidative sulfonamidation of O-containing vinylsilanes. A new route to novel heterocycles and amidines
T2 - Journal of Organometallic Chemistry
AU - Moskalik, Mikhail Yu
AU - Garagan, Ivan A
AU - Ganin, Anton S
AU - Astakhova, V V
AU - Sterkhova, Irina
AU - Shainyan, Bagrat A.
PY - 2021
DA - 2021/10/01
PB - Elsevier
SP - 122010
VL - 951
SN - 0022-328X
SN - 1872-8561
ER -
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@article{2021_Moskalik,
author = {Mikhail Yu Moskalik and Ivan A Garagan and Anton S Ganin and V V Astakhova and Irina Sterkhova and Bagrat A. Shainyan},
title = {Oxidative sulfonamidation of O-containing vinylsilanes. A new route to novel heterocycles and amidines},
journal = {Journal of Organometallic Chemistry},
year = {2021},
volume = {951},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/j.jorganchem.2021.122010},
pages = {122010},
doi = {10.1016/j.jorganchem.2021.122010}
}