Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond
Publication type: Journal Article
Publication date: 2019-11-01
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31674792
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
Trifluorodiazoethane is a widely explored trifluoroethylating reagent, which is suitable for the preparation of a large number of fluorine-containing organic molecules. Nevertheless, CF3CHN2 has some disadvantages, such as volatility, storage instability, toxicity, and explosiveness. We report the application of trifluoroacetaldehyde N-tosylhydrazone as a CF3CHN2 precursor capable of generating in situ trifluorodiazoethane under mild basic conditions. Copper-catalyzed P-H, O-H, S-H, and C-H insertion reactions of trifluoroacetaldehyde N-tosylhydrazone revealed its wide applicability in the synthesis of trifluoroethyl-containing substances.
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28
Total citations:
28
Citations from 2024:
11
(39.29%)
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Ostrovskii V. S., Beletskaya I. P., Titanyuk I. D. Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond // Organic Letters. 2019. Vol. 21. No. 22. pp. 9080-9083.
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Ostrovskii V. S., Beletskaya I. P., Titanyuk I. D. Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond // Organic Letters. 2019. Vol. 21. No. 22. pp. 9080-9083.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.9b03471
UR - https://doi.org/10.1021/acs.orglett.9b03471
TI - Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond
T2 - Organic Letters
AU - Ostrovskii, Vladimir S
AU - Beletskaya, Irina P.
AU - Titanyuk, Igor D
PY - 2019
DA - 2019/11/01
PB - American Chemical Society (ACS)
SP - 9080-9083
IS - 22
VL - 21
PMID - 31674792
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2019_Ostrovskii,
author = {Vladimir S Ostrovskii and Irina P. Beletskaya and Igor D Titanyuk},
title = {Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.orglett.9b03471},
number = {22},
pages = {9080--9083},
doi = {10.1021/acs.orglett.9b03471}
}
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Ostrovskii, Vladimir S., et al. “Trifluoroacetaldehyde N-Tosylhydrazone as a Precursor of Trifluorodiazoethane in Reactions of Insertion into the Heteroatom-Hydrogen Bond.” Organic Letters, vol. 21, no. 22, Nov. 2019, pp. 9080-9083. https://doi.org/10.1021/acs.orglett.9b03471.
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