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Direct N- and C-vinylation with trimethoxyvinylsilane

Pavel Arsenyan 1
Pavel Arsenyan
, 
Alla Petrenko 1
Alla Petrenko
, 
Edgars Paegle 1
Edgars Paegle
, 
Sergey Belyakov 1
Sergey Belyakov
10.1016/j.mencom.2011.11.011
Published 2011-11-10
Communication , Volume 21, Issue 6, 326-328
12
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Arsenyan P. et al. Direct N- and C-vinylation with trimethoxyvinylsilane // Mendeleev Communications. 2011. Vol. 21. No. 6. pp. 326-328.
GOST all authors (up to 50) Copy
Arsenyan P., Petrenko A., Paegle E., Belyakov S. Direct N- and C-vinylation with trimethoxyvinylsilane // Mendeleev Communications. 2011. Vol. 21. No. 6. pp. 326-328.
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TY - JOUR
DO - 10.1016/j.mencom.2011.11.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.011
TI - Direct N- and C-vinylation with trimethoxyvinylsilane
T2 - Mendeleev Communications
AU - Arsenyan, Pavel
AU - Petrenko, Alla
AU - Paegle, Edgars
AU - Belyakov, Sergey
PY - 2011
DA - 2011/11/10
PB - Mendeleev Communications
SP - 326-328
IS - 6
VL - 21
ER -
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@article{2011_Arsenyan,
author = {Pavel Arsenyan and Alla Petrenko and Edgars Paegle and Sergey Belyakov},
title = {Direct N- and C-vinylation with trimethoxyvinylsilane},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.011},
number = {6},
pages = {326--328},
doi = {10.1016/j.mencom.2011.11.011}
}
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Arsenyan, Pavel, et al. “Direct N- and C-vinylation with trimethoxyvinylsilane.” Mendeleev Communications, vol. 21, no. 6, Nov. 2011, pp. 326-328. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.11.011.

Keywords

Catalysis; Copper(II) acetate; Nucleobase; Nucleoside; Silane

Abstract

Treatment of nucleobases, nucleosides, 5-membered N-heterocycles and terminal alkynes with trimethoxyvinylsilane in the presence of copper(II) acetate–TBAF system as catalyst affords the vinylation products.

References

2.
(a) P. Y. S. Lam, C.G. Clark, S. Saubern, J. Adams, K. Averill, D.M. T. Chan and A. P. Combs, Synlett, 2000, 674;
3.
New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation
Lam P.Y., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M., Combs A.
Tetrahedron Letters, 1998
5.
New N- and O-arylations with phenylboronic acids and cupric acetate
Chan D.M., Monaco K.L., Wang R., Winters M.P.
Tetrahedron Letters, 1998
7.
Copper-promoted CN bond cross-coupling with phenylstannane
Lam P.Y., Vincent G., Bonne D., Clark C.G.
Tetrahedron Letters, 2002
9.
Synthesis and structure of 1,3-divinyl-5-halouracils
Voronkov M.G., Stepanova Z.V., Afonin A.V., Voronov V.K.
Russian Chemical Bulletin, 1987
10.
(b) Z. V. Stepanova, G.G. Skvortsova, V.K. Voronov and A. V. Afonin, Khim. Geterotsikl. Soedin., 1986, 567. [Chem. Heterocycl. Compd. (Engl. Transl.), 1986, 22, 469].
11.
Synthesis of Dihydroisoxazole Nucleoside and Nucleotide Analogs
Gi H., Xiang Y., Schinazi R.F., Zhao K.
Journal of Organic Chemistry, 1997
12.
A Convenient Method for the Synthesis of N-Vinyl Derivatives of Nucleobases
Procopio A., Dalpozzo R., Nino A., Maiuolo L., Romeo R., Sindona G.
Synthesis, 2004
13.
Palladium-catalyzed stereocontrolled vinylation of azoles and phenothiazine
Lebedev A.Y., Izmer V.V., Kazyul'kin D.N., Beletskaya I.P., Voskoboynikov A.Z.
Organic Letters, 2002
15.
Organoinorganic composites based on tetraethoxysilane and nitrogen polybases
Shaglaeva N.S., Lebedeva O.V., Pozhidaev Y.N., Sultangareev R.G., Bochkareva S.S., Es’kova L.A.
Russian Journal of Physical Chemistry A, 2007
17.
(e) B. N. Laskorin, N.G. Zhukova, O.N. Grishina, G.G. Skvortsova, E.S. Domnina and S. A. Ostrovskii, Zh. Prikl. Khim., 1982, 55, 506 [J. Appl. Chem. USSR (Engl. Transl.), 1982, 55, 555];
18.
(f) V. N. Voropaev, E.S. Domnina, N.P. Glazkova and G. G. Skvortsova, Zh. Prikl. Khim., 1983, 56, 2123 [J. Appl. Chem. USSR (Engl. Transl.), 1983, 56, 2289];
20.
(h) V. F. Kukharev, V.K. Stankevich, G.R. Klimenko, V.G. Popova, L.E. Belozerov and E. S. Domnina, Zh. Prikl. Khim., 1984, 57, 1980. [J. Appl. Chem. USSR (Engl. Transl.), 1984, 57, 2137].
21.
SIR97: a new tool for crystal structure determination and refinement
Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G., Polidori G., Spagna R.
Journal of Applied Crystallography, 1999
22.
S. Mackay, W. Dong, C. Edwards, A. Henderson, C.J. Gilmore, N. Stewart, K. Shankland and A. Donald, maXus, Integrated Crystallography Software, Bruker-Nonius and University of Glasgow, 2003.
23.
Synthesis of α-Hydroxyallenes by Copper-Catalyzed SN2′ Substitution of Propargylic Dioxolanones
Tang X., Woodward S., Krause N.
European Journal of Organic Chemistry, 2009
24.
Conjugated Enynes as a New Type of Substrates for Olefin Metathesis
Kang B., Kim D., Do Y., Chang S.
Organic Letters, 2003
25.
Cobalt-catalyzed hydrohydrazination of dienes and enynes: access to allylic and propargylic hydrazides.
Waser J., González-Gómez J.C., Nambu H., Huber P., Carreira E.M.
Organic Letters, 2005
26.
Competitive 1,2- and 1,5-Hydrogen Shifts Following 2-Vinylbiphenyl Photocyclization
Lewis F.D., Sajimon M.C., Zuo X., Rubin M., Gevorgyan V.
Journal of Organic Chemistry, 2005
27.
(e) I. N. Nazarov, Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk, 1938, 704 (in Russian);
28.
(f) B. A. Trofimov, L.N. Sobenina, S.E. Korostova, A.I. Mikhaleva, N.I. Shishov, V.D. Feldman, S.G. Shevchenko and A. N. Vasilev, Zh. Prikl. Khim., 1987, 60, 1366 (in Russian);