Home / Publications / Hydroxyl-directed trifluoromethylation of hydrazones

Hydroxyl-directed trifluoromethylation of hydrazones

, 
Vitalij Vladimirovich Levin 1
Vitalij Vladimirovich Levin
, 
Pavel Alekseevich Belyakov 1
Pavel Alekseevich Belyakov
, 
Alexander Aleksandrovich Korlyukov 2
Alexander Aleksandrovich Korlyukov
, 
Marina Ivanovna Struchkova 1
Marina Ivanovna Struchkova
, 
Vladimir Alexandrovich Tartakovsky 1
Vladimir Alexandrovich Tartakovsky
10.1016/j.mencom.2009.05.009
Published 2009-05-08
Communication , Volume 19, Issue 3, 141-143
9
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Dilman A. D. et al. Hydroxyl-directed trifluoromethylation of hydrazones // Mendeleev Communications. 2009. Vol. 19. No. 3. pp. 141-143.
GOST all authors (up to 50) Copy
Dilman A. D., Levin V. V., Belyakov P. A., Korlyukov A. A., Struchkova M. I., Tartakovsky V. A. Hydroxyl-directed trifluoromethylation of hydrazones // Mendeleev Communications. 2009. Vol. 19. No. 3. pp. 141-143.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2009.05.009
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.009
TI - Hydroxyl-directed trifluoromethylation of hydrazones
T2 - Mendeleev Communications
AU - Dilman, Alexander Davidovich
AU - Levin, Vitalij Vladimirovich
AU - Belyakov, Pavel Alekseevich
AU - Korlyukov, Alexander Aleksandrovich
AU - Struchkova, Marina Ivanovna
AU - Tartakovsky, Vladimir Alexandrovich
PY - 2009
DA - 2009/05/08
PB - Mendeleev Communications
SP - 141-143
IS - 3
VL - 19
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2009_Dilman,
author = {Alexander Davidovich Dilman and Vitalij Vladimirovich Levin and Pavel Alekseevich Belyakov and Alexander Aleksandrovich Korlyukov and Marina Ivanovna Struchkova and Vladimir Alexandrovich Tartakovsky},
title = {Hydroxyl-directed trifluoromethylation of hydrazones},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.009},
number = {3},
pages = {141--143},
doi = {10.1016/j.mencom.2009.05.009}
}
MLA
Cite this
MLA Copy
Dilman, Alexander Davidovich, et al. “Hydroxyl-directed trifluoromethylation of hydrazones.” Mendeleev Communications, vol. 19, no. 3, May. 2009, pp. 141-143. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.05.009.

Abstract

The trifluoromethylation of hydrazones derived from salicyl aldehydes and N-aminopiperidine and N-aminomorpholine through the generation of chelate difluoroboron complexes, which subsequently interact with Me3SiCF3 in the presence of sodium acetate, has been developed.

References

1.
Perfluoroalkylation with Organosilicon Reagents
Prakash G.K., Yudin A.K.
Chemical Reviews, 1997
2.
Nucleophilic trifluoromethylation tamed
Prakash G.K., Mandal M.
Journal of Fluorine Chemistry, 2001
5.
Recent advances in enantioselective trifluoromethylation reactions
Shibata N., Mizuta S., Kawai H.
Tetrahedron Asymmetry, 2008
6.
Facile Synthesis of TMS-Protected Trifluoromethylated Alcohols Using Trifluoromethyltrimethylsilane (TMSCF3) and Various Nucleophilic Catalysts in DMF
Prakash G.K., Panja C., Vaghoo H., Surampudi V., Kultyshev R., Mandal M., Rasul G., Mathew T., Olah G.A.
Journal of Organic Chemistry, 2006
7.
Lewis Base-Catalyzed Perfluoroalkylation of Carbonyl Compounds and Imines with (Perfluoroalkyl)trimethylsilane
Kawano Y., Kaneko N., Mukaiyama T.
Bulletin of the Chemical Society of Japan, 2006
8.
Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones.
Mizuta S., Shibata N., Akiti S., Fujimoto H., Nakamura S., Toru T.
Organic Letters, 2007
9.
An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols
Fustero S., Albert L., Aceña J.L., Sanz-Cervera J.F., Asensio A.
Organic Letters, 2008
10.
Stereoselective addition of CF3SiMe3 on azirines. Synthesis of (E)-aziridines
Félix C.P., Khatimi N., Laurent A.J.
Tetrahedron Letters, 1994
12.
Nucleophilic Trifluoromethylation of N-Tosyl Aldimines
Prakash G.K., Mandal M., Olah G.A.
Synlett, 2001
14.
Trifluoromethylation of non-activated aldimines with trimethyl(trifluoromethyl)silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route
Kirij N.V., Babadzhanova L.A., Movchun V.N., Yagupolskii Y.L., Tyrra W., Naumann D., Fischer H.T., Scherer H.
Journal of Fluorine Chemistry, 2008
15.
Extending the scope of Ruppert's reagent: trifluoromethylation of imines
Blazejewski J., Anselmi E., Wilmshurst M.P.
Tetrahedron Letters, 1999
16.
Preparation of (1R,1′R)-1,1′-(anthracene-9,10-diyl)bis(2,2,2-trifluoroethanamine): a chiral diamine with low basicity
Estivill C., Mendizabal J., Virgili A., Monteagudo E., Flor T., Sánchez-Ferrando F., Alvarez-Larena A., Piniella J.F.
Tetrahedron, 2009
17.
Nucleophilic Trifluoromethylation of Imines under Acidic Conditions
Levin V.V., Dilman A.D., Belyakov P.A., Struchkova M.I., Tartakovsky V.A.
European Journal of Organic Chemistry, 2008
18.
Nucleophilic fluoroalkylation of iminium salts
Levin V.V., Kozlov M.A., Song Y., Dilman A.D., Belyakov P.A., Struchkova M.I., Tartakovsky V.A.
Tetrahedron Letters, 2008
19.
The Trifluoroethylamine Function as Peptide Bond Replacement
Sani M., Volonterio A., Zanda M.
ChemMedChem, 2007
20.
Primary amides as selective inhibitors of cathepsin K
Léger S., Bayly C.I., Black W.C., Desmarais S., Falgueyret J., Massé F., Percival M.D., Truchon J.
Bioorganic and Medicinal Chemistry Letters, 2007
23.
The chemistry of trifluoromethyl imines and related acetals derived from fluoral
Bégué J., Bonnet-Delpon D., Crousse B., Legros J.
Chemical Society Reviews, 2005
25.
A New Strategy for the Synthesis of Optically Pure β-Fluoroalkyl β-Amino Acid Derivatives
Fustero S., del Pozo C., Catalán S., Alemán J., Parra A., Marcos V., Ruano J.L.
Organic Letters, 2009
26.
Chiral sulfoxide controlled asymmetric additions to CN double bond. An efficient approach to stereochemically defined α-fluoroalkyl amino compounds
Bravo P., Guidetti M., Viani F., Zanda M., Markovsky A.L., Sorochinsky A.E., Soloshonok I.V., Soloshonok V.A.
Tetrahedron, 1998
27.
Stereoselective Additions of α-Lithiated Alkyl-p-tolylsulfoxides to N-PMP(fluoroalkyl)aldimines. An Efficient Approach to Enantiomerically Pure Fluoro Amino Compounds
Bravo P., Farina A., Kukhar V.P., Markovsky A.L., Meille S.V., Soloshonok V.A., Sorochinsky A.E., Viani F., Zanda M., Zappalà C.
Journal of Organic Chemistry, 1997
28.
Diastereoselective Reductive Amination of Aryl Trifluoromethyl Ketones and α-Amino Esters
Hughes G., Devine P., Naber J., O'Shea P., Foster B., McKay D., Volante R. .
Angewandte Chemie - International Edition, 2007
32.
Kinetics and mechanism of triethylamine-catalyzed 1,3-proton shift
Nagy P., Ueki H., Berbasov D.O., Soloshonok V.A.
Journal of Fluorine Chemistry, 2008
37.
S. Kim and J. Y. Yoon, in Compounds with Two Carbon-Heteroatom Bonds: Heteroatom Analogues of Aldehydes and Ketones, eds. A. Pawda and D. Bellus, Georg Thieme Verlag, Stuttgart–New York, 2004, pp. 671–722.
38.
Trifluoromethylation of Salicyl Aldimines
Dilman A.D., Arkhipov D.E., Levin V.V., Belyakov P.A., Korlyukov A.A., Struchkova M.I., Tartakovsky V.A.
Journal of Organic Chemistry, 2007
39.
Trifluoromethylation of N-Benzoylhydrazones
Dilman A.D., Arkhipov D.E., Levin V.V., Belyakov P.A., Korlyukov A.A., Struchkova M.I., Tartakovsky V.A.
Journal of Organic Chemistry, 2008
40.
Notes: Alkylidene- and Arylideneaminomorpholines
Wiley R., White H., Irick G.
Journal of Organic Chemistry, 1959
41.
10.1016/j.mencom.2009.05.009_bib14
Bren
Zh. Org. Khim., 1976