Modular Construction of Functionalized 2-CF3-Indoles
Publication type: Journal Article
Publication date: 2021-07-12
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
34251819
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The reaction of α-CF3-β-(2-nitroaryl)enamines with benzaldehydes led to nitro-substituted α,β-diaryl-CF3-enones in high yield. Subsequent reduction of the nitro-group to the amino moiety by the Pd/C-NH4HCO2 system resulted in intramolecular cyclization to form a 5-membered hemiaminal which is stabilized by the presence of a CF3-group. The reaction of this hemiaminal with various nucleophiles afforded functionalized 2-CF3-indoles isolated in up to quantitative yields. High efficiency and broad synthetic scope of all steps of the sequence were demonstrated. A possible mechanism of the reaction is discussed.
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14
Total citations:
14
Citations from 2024:
9
(64.29%)
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GOST
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Muzalevskiy V. M., Sizova Z. A., Nenajdenko V. G. Modular Construction of Functionalized 2-CF3-Indoles // Organic Letters. 2021. Vol. 23. No. 15. pp. 5973-5977.
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Muzalevskiy V. M., Sizova Z. A., Nenajdenko V. G. Modular Construction of Functionalized 2-CF3-Indoles // Organic Letters. 2021. Vol. 23. No. 15. pp. 5973-5977.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.1c02061
UR - https://doi.org/10.1021/acs.orglett.1c02061
TI - Modular Construction of Functionalized 2-CF3-Indoles
T2 - Organic Letters
AU - Muzalevskiy, Vasily M.
AU - Sizova, Zoia A
AU - Nenajdenko, Valentine G.
PY - 2021
DA - 2021/07/12
PB - American Chemical Society (ACS)
SP - 5973-5977
IS - 15
VL - 23
PMID - 34251819
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Muzalevskiy,
author = {Vasily M. Muzalevskiy and Zoia A Sizova and Valentine G. Nenajdenko},
title = {Modular Construction of Functionalized 2-CF3-Indoles},
journal = {Organic Letters},
year = {2021},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.1c02061},
number = {15},
pages = {5973--5977},
doi = {10.1021/acs.orglett.1c02061}
}
Cite this
MLA
Copy
Muzalevskiy, Vasily M., et al. “Modular Construction of Functionalized 2-CF3-Indoles.” Organic Letters, vol. 23, no. 15, Jul. 2021, pp. 5973-5977. https://doi.org/10.1021/acs.orglett.1c02061.