Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane
Publication type: Journal Article
Publication date: 2013-06-17
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The ruthenium complex [Cp(iPr3P)Ru(NCCH3)2]+ (1) catalyzes the regioselective hydrosilylation of pyridines to 1,4-dihydropyridines. Substitution in the 3- and 5-positions is tolerated, whereas pyridines with substituents in the 2-, 4-, and 6-positions are not reduced. Reduction of functionalized pyridines having keto and ester substituents results in a mixture of products. N-Silyl-1,4-dihydropyridine reacts with ketones and aldehydes to give products of N–Si addition across the C═O bond. Hydrosilylation of pyridine in acetone results quantitatively in the addition product PhMe2SiO–CMe2–NC5H6, which decomposes in hexane to give the parent dihydropyridine HNC5H6. The phenanthroline complex [Cp(phen)Ru(NCCH3)2]+ (10) catalyzes regioselective 1,4-reduction of phenanthroline by a 3–4-fold excess of silane/water or silane/alcohol mixtures. The Cp* analogue [Cp*(phen)Ru(NCCH3)2]+ (9) catalyzes 1,4-regioselective monohydrosilylation of phenanthroline, quinoline, acridine, and 1,3,5-triazine and the 1,2-reduction ...
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Total citations:
61
Citations from 2024:
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(11.48%)
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Lee S. H., Gutsulyak D. V., Nikonov G. I. Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane // Organometallics. 2013. Vol. 32. No. 16. pp. 4457-4464.
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Lee S. H., Gutsulyak D. V., Nikonov G. I. Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane // Organometallics. 2013. Vol. 32. No. 16. pp. 4457-4464.
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RIS
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TY - JOUR
DO - 10.1021/om400269q
UR - https://doi.org/10.1021/om400269q
TI - Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane
T2 - Organometallics
AU - Lee, Sun Hwa
AU - Gutsulyak, Dmitry V
AU - Nikonov, G. I.
PY - 2013
DA - 2013/06/17
PB - American Chemical Society (ACS)
SP - 4457-4464
IS - 16
VL - 32
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2013_Lee,
author = {Sun Hwa Lee and Dmitry V Gutsulyak and G. I. Nikonov},
title = {Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane},
journal = {Organometallics},
year = {2013},
volume = {32},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/om400269q},
number = {16},
pages = {4457--4464},
doi = {10.1021/om400269q}
}
Cite this
MLA
Copy
Lee, Sun Hwa, et al. “Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane.” Organometallics, vol. 32, no. 16, Jun. 2013, pp. 4457-4464. https://doi.org/10.1021/om400269q.