Home / Publications / Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity

Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
, 
Svetlana Filippovna Malysheva 1
Svetlana Filippovna Malysheva
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Natalia Alekseevna Belogorlova 1
Natalia Alekseevna Belogorlova
, 
Sergey Franzevich Vasilevskii 2
Sergey Franzevich Vasilevskii
, 
Vladimir Borisovich Kobychev 1
Vladimir Borisovich Kobychev
, 
Boris Genad'evch Sukhov 1
Boris Genad'evch Sukhov
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
10.1016/j.mencom.2007.05.017
Published 2007-05-03
Communication , Volume 17, Issue 3, 181-182
17
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Trofimov B. A. et al. Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity // Mendeleev Communications. 2007. Vol. 17. No. 3. pp. 181-182.
GOST all authors (up to 50) Copy
Trofimov B. A., Malysheva S. F., Gusarova N. K., Belogorlova N. A., Vasilevskii S. F., Kobychev V. B., Sukhov B. G., Ushakov I. A. Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity // Mendeleev Communications. 2007. Vol. 17. No. 3. pp. 181-182.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2007.05.017
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.017
TI - Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Malysheva, Svetlana Filippovna
AU - Gusarova, Nina Kuzminichna
AU - Belogorlova, Natalia Alekseevna
AU - Vasilevskii, Sergey Franzevich
AU - Kobychev, Vladimir Borisovich
AU - Sukhov, Boris Genad'evch
AU - Ushakov, Igor Alekseevich
PY - 2007
DA - 2007/05/03
PB - Mendeleev Communications
SP - 181-182
IS - 3
VL - 17
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2007_Trofimov,
author = {Boris Aleksandrovich Trofimov and Svetlana Filippovna Malysheva and Nina Kuzminichna Gusarova and Natalia Alekseevna Belogorlova and Sergey Franzevich Vasilevskii and Vladimir Borisovich Kobychev and Boris Genad'evch Sukhov and Igor Alekseevich Ushakov},
title = {Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.017},
number = {3},
pages = {181--182},
doi = {10.1016/j.mencom.2007.05.017}
}
MLA
Cite this
MLA Copy
Trofimov, Boris Aleksandrovich, et al. “Free-radical addition of phosphine sulfides to aryl and hetaryl acetylenes: unprecedented stereoselectivity.” Mendeleev Communications, vol. 17, no. 3, May. 2007, pp. 181-182. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.05.017.

Abstract

Secondary phosphine sulfides react stereo- and regioselectively with aryl and hetaryl acetylenes in the presence of radical initiators (AIBN, 60–65 °C) in the anti-Markovnikov mode giving Z-isomers of the corresponding monoadducts in high yields.

References

1.
J. I. Dickstein and S. I.Miller, in The Chemistry of the Carbon–Carbon Triple Bond, ed. S. Patai, John Wiley, Chichester, 1978, part 2, p. 813;
3.
B. A. Trofimov, in Sovremennye problemy organicheskoi khimii (Modern Problems of Organic Chemistry), VVM, St. Petersburg, 2004, p. 121 (in Russian);
6.
Stereoselective addition of diphenylphosphine to substituted diphenylethynes: synthetic, NMR and X-ray crystallographic studies
Bookham J.L., Smithies D.M., Wright A., Thornton-Pett M., McFarlane W.
Journal of the Chemical Society Dalton Transactions, 1998
8.
Approaches to water-soluble phosphines
Heesche-Wagner K., Mitchell T.N.
Journal of Organometallic Chemistry, 1994
9.
Radical addition reactions of chiral phosphorus hydrides
Jessop C.M., Parsons A.F., Routledge A., Irvine D.J.
Tetrahedron Asymmetry, 2003
10.
Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
Alonso F., Beletskaya I.P., Yus M.
Chemical Reviews, 2004
11.
Asymmetric Catalysis in Organic Synthesis, ed. R. Noyori, John Wiley & Sons, New York, 1994;
12.
Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999;
13.
Catalytic Asymmetric Synthesis, ed. I. Ojima, 2nd edn., VCH Pubishers, Weinheim, 2000.
18.
Triazole-Based Monophosphine Ligands for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Chlorides
Dai Q., Gao W., Liu D., Kapes L.M., Zhang X.
Journal of Organic Chemistry, 2006
20.
10.1016/j.mencom.2007.05.017_bib6_1
Gubin
Izv. Akad. Nauk, Ser. Khim., 2005
21.
Mechanistic Study of Precursor Evolution in Colloidal Group II−VI Semiconductor Nanocrystal Synthesis
Liu H., Owen J.S., Alivisatos A.P.
Journal of the American Chemical Society, 2006