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Synthesis of S-difluoromethyl dithiocarbamates

, 
Anton Sergeyevich Maslov 1, 2
Anton Sergeyevich Maslov
, 
Marina Ivanovna Struchkova 1
Marina Ivanovna Struchkova
, 
Dmitry Evgen'evich Arkhipov 3
Dmitry Evgen'evich Arkhipov
, 
10.1016/j.mencom.2015.11.018
Published 2015-11-09
Communication , Volume 25, Issue 6, 452-453
8
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Smirnov V. O. et al. Synthesis of S-difluoromethyl dithiocarbamates // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 452-453.
GOST all authors (up to 50) Copy
Smirnov V. O., Maslov A. S., Struchkova M. I., Arkhipov D. E., Dilman A. D. Synthesis of S-difluoromethyl dithiocarbamates // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 452-453.
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TY - JOUR
DO - 10.1016/j.mencom.2015.11.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.018
TI - Synthesis of S-difluoromethyl dithiocarbamates
T2 - Mendeleev Communications
AU - Smirnov, Vladimir Olgerdovich
AU - Maslov, Anton Sergeyevich
AU - Struchkova, Marina Ivanovna
AU - Arkhipov, Dmitry Evgen'evich
AU - Dilman, Alexander Davidovich
PY - 2015
DA - 2015/11/09
PB - Mendeleev Communications
SP - 452-453
IS - 6
VL - 25
ER -
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@article{2015_Smirnov,
author = {Vladimir Olgerdovich Smirnov and Anton Sergeyevich Maslov and Marina Ivanovna Struchkova and Dmitry Evgen'evich Arkhipov and Alexander Davidovich Dilman},
title = {Synthesis of S-difluoromethyl dithiocarbamates},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.018},
number = {6},
pages = {452--453},
doi = {10.1016/j.mencom.2015.11.018}
}
MLA
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MLA Copy
Smirnov, Vladimir Olgerdovich, et al. “Synthesis of S-difluoromethyl dithiocarbamates.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 452-453. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.018.

Abstract

A method for preparation of S-difluoromethyl dithiocarbamates has been developed, which involves the treatment of secondary amines with carbon disulfide in methanol followed by S-difluoromethylation of the intermediate dithiocarbamate anion with difluorocarbene generated from (bromodifluoromethyl)trimethylsilane.

References

1.
10.1016/j.mencom.2015.11.018_sbref0005a
Wang
Chem. Rev, 2014
2.
Fluorine in Medicinal Chemistry and Chemical Biology,ed. I. Ojima, John Wiley & Sons, Chichester, 2009.
3.
10.1016/j.mencom.2015.11.018_sbref0005c
Begue
Wiley-VCH Weinheim, 2008
4.
Development of new methods in modern selective organic synthesis: Preparation of functionalized molecules with atomic precision
Ananikov V.P., Khemchyan L.L., Ivanova Y.V., Bukhtiyarov V.I., Sorokin A.M., Prosvirin I.P., Vatsadze S.Z., Medved'ko A.V., Nuriev V.N., Dilman A.D., Levin V.V., Koptyug I.V., Kovtunov K.V., Zhivonitko V.V., Likholobov V.A., et. al.
Russian Chemical Reviews, 2014
5.
Perfluoroalkylation with Organosilicon Reagents
Prakash G.K., Yudin A.K.
Chemical Reviews, 1997
7.
Nucleophilic Trifluoromethylation of C=N Bonds
Dilman A.D., Levin V.V.
European Journal of Organic Chemistry, 2011
9.
Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
Charpentier J., Früh N., Togni A.
Chemical Reviews, 2014
11.
A "Renaissance" in radical trifluoromethylation.
Studer A.
Angewandte Chemie - International Edition, 2012
12.
Romanov A.R., Rulev A.Y., Ushakov I.A., Muzalevskiy V.M., Nenajdenko V.G.
Mendeleev Communications, 2014
13.
Muzalevskiy V.M., Iskandarov A.A., Nenajdenko V.G.
Mendeleev Communications, 2014
14.
Hydrogen Bond Donor Properties of the Difluoromethyl Group
Erickson J.A., McLoughlin J.I.
Journal of Organic Chemistry, 1995
17.
Sandmeyer difluoromethylation of (hetero-)arenediazonium salts.
Matheis C., Jouvin K., Goossen L.J.
Organic Letters, 2014
18.
Copper-mediated difluoromethylation of aryl and vinyl iodides.
Fier P.S., Hartwig J.F.
Journal of the American Chemical Society, 2012
19.
Copper-mediated difluoromethylation of (hetero)aryl iodides and β-styryl halides with tributyl(difluoromethyl)stannane.
Prakash G.K., Ganesh S.K., Jones J., Kulkarni A., Masood K., Swabeck J.K., Olah G.A.
Angewandte Chemie - International Edition, 2012
20.
10.1016/j.mencom.2015.11.018_sbref0030e
Fujiwara
J. Am. Chem. Soc, 2012
21.
Difluoromethylene Phosphabetaine as an Equivalent of Difluoromethyl Carbanion
Levin V.V., Trifonov A.L., Zemtsov A.A., Struchkova M.I., Arkhipov D.E., Dilman A.D.
Organic Letters, 2014
22.
10.1016/j.mencom.2015.11.018_sbref0035a
Prakash
Org. Lett, 2007
24.
10.1016/j.mencom.2015.11.018_sbref0035c
Wang
Chin. J. Chem, 2011
25.
10.1016/j.mencom.2015.11.018_sbref0035d
Li
Angew. Chem. Int., 2013
26.
Synthesis of Difluoromethyl Ethers with Difluoromethyltriflate
Fier P.S., Hartwig J.F.
Angewandte Chemie - International Edition, 2013
27.
10.1016/j.mencom.2015.11.018_bib0040
Hudlický
Org. React., 1988
28.
Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents
Li R., Wang H., Li Y., Wang Z., Wang X., Wang Y., Ge Z., Li R.
European Journal of Medicinal Chemistry, 2015
29.
Dithiocarbamates Strongly Inhibit Carbonic Anhydrases and Show Antiglaucoma Action in Vivo
Carta F., Aggarwal M., Maresca A., Scozzafava A., McKenna R., Masini E., Supuran C.T.
Journal of Medicinal Chemistry, 2012
30.
Dicationic dithiocarbamate carbapenems with anti-MRSA activity
Imamura H., Ohtake N., Jona H., Shimizu A., Moriya M., Sato H., Sugimoto Y., Ikeura C., Kiyonaga H., Nakano M., Nagano R., Abe S., Yamada K., Hashizume T., Morishima H., et. al.
Bioorganic and Medicinal Chemistry, 2001
31.
Synthesis and Antifungal Activity of Novel Bis(dithiocarbamate) Derivatives of Glycerol
Len C., Boulogne-Merlot A., Postel D., Ronco G., Villa P., Goubert C., Jeufrault E., Mathon B., Simon H.
Journal of Agricultural and Food Chemistry, 1996
32.
Dithiocarbamate-substituted gem-difluorinated silicon reagent: generation and addition to aldehydes
Maslov A.S., Smirnov V.O., Struchkova M.I., Arkhipov D.E., Dilman A.D.
Tetrahedron Letters, 2015
35.
10.1016/j.mencom.2015.11.018_bib0060
Kosobokov
J. Org. Chem., 2012
36.
Reactions of Difluorocarbene with Organozinc Reagents
Levin V.V., Zemtsov A.A., Struchkova M.I., Dilman A.D.
Organic Letters, 2013
37.
Nucleophilic Bromo- and Iododifluoromethylation of Aldehydes
Kosobokov M.D., Levin V.V., Struchkova M.I., Dilman A.D.
Organic Letters, 2014
38.
Geminal silicon/zinc reagent as an equivalent of difluoromethylene bis-carbanion.
Kosobokov M.D., Levin V.V., Zemtsov A.A., Struchkova M.I., Korlyukov A.A., Arkhipov D.E., Dilman A.D.
Organic Letters, 2014
39.
Nucleophilic Bromodifluoromethylation of Iminium Ions
Tsymbal A.V., Kosobokov M.D., Levin V.V., Struchkova M.I., Dilman A.D.
Journal of Organic Chemistry, 2014
40.
Difluorohomologation of Ketones
Kosobokov M.D., Levin V.V., Struchkova M.I., Dilman A.D.
Organic Letters, 2015
41.
Halogenative Difluorohomologation of Ketones
Fedorov O.V., Kosobokov M.D., Levin V.V., Struchkova M.I., Dilman A.D.
Journal of Organic Chemistry, 2015
42.
10.1016/j.mencom.2015.11.018_sbref0065g
Song
Org. Lett, 2015
43.
10.1016/j.mencom.2015.11.018_sbref0065h
Levin
J. Org. Chem, 2015