Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes
Publication type: Journal Article
Publication date: 2020-02-05
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
32019300
Organic Chemistry
Abstract
Aldimines react with aryl- and hetarylacetylenes in the presence of KOBut/dimethyl sulfoxide (DMSO) or NaOBut/DMSO systems under exceptionally mild conditions (14 °C, 1 h) to afford C-H-vinylated products, 1-azadienes of E configuration relative to the C-C bond, in up to 72% yield. Vinylation involves the unprecedentedly fast multiposition proton transfer in the intermediate adducts of acetylene to the C═N bond. This new Csp2-Csp2 bond-forming reaction opens a straightforward pot-, atom-, step-, and energy-economic access to synthetically valuable 1-azadienes.
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Total citations:
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Citations from 2024:
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GOST
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Schmidt E. Yu. et al. Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3417-3425.
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Schmidt E. Yu., Bidusenko I. A., Protsuk N. I., Demyanov Y. V., Ushakov I., Vashchenko A. V., Trofimov B. A. Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes // Journal of Organic Chemistry. 2020. Vol. 85. No. 5. pp. 3417-3425.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b03192
UR - https://doi.org/10.1021/acs.joc.9b03192
TI - Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes
T2 - Journal of Organic Chemistry
AU - Schmidt, Elena Yu
AU - Bidusenko, Ivan A
AU - Protsuk, Nadezhda I
AU - Demyanov, Yan V
AU - Ushakov, Igor
AU - Vashchenko, Alexander V.
AU - Trofimov, B. A.
PY - 2020
DA - 2020/02/05
PB - American Chemical Society (ACS)
SP - 3417-3425
IS - 5
VL - 85
PMID - 32019300
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Schmidt,
author = {Elena Yu Schmidt and Ivan A Bidusenko and Nadezhda I Protsuk and Yan V Demyanov and Igor Ushakov and Alexander V. Vashchenko and B. A. Trofimov},
title = {Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.joc.9b03192},
number = {5},
pages = {3417--3425},
doi = {10.1021/acs.joc.9b03192}
}
Cite this
MLA
Copy
Schmidt, Elena Yu., et al. “Transition-Metal-Free Superbase-Catalyzed C–H Vinylation of Aldimines with Acetylenes to 1-Azadienes.” Journal of Organic Chemistry, vol. 85, no. 5, Feb. 2020, pp. 3417-3425. https://doi.org/10.1021/acs.joc.9b03192.