Active-alkali metal promoted reductive desulfurization of dibenzothiophene and its hindered analogues

作者: Mario Pittalis , Ugo Azzena , Luisa Pisano

DOI: 10.1016/J.TET.2012.10.044

关键词:

摘要: Dibenzothiophene and some related organosulfur compounds are efficiently reductively desulfurized under mild reaction conditions, with Na and/or Li metal in the presence of a catalytic amount tetraphenylethylene THF at room temperature. This simple methodology was applied to synthesis several substituted biphenyls, thus realizing connection between directing properties sulfur atom dibenzothiophene efficiency 1,2-dianions tetraphenylethane as homogenous electron transfer reagents.

参考文章(39)
Ugo Azzena, Florian Kondrot, Luisa Pisano, Mario Pittalis, A green solvent approach to the chemistry of 1,2‐diaryl‐1,2‐disodioethanes Applied Organometallic Chemistry. ,vol. 26, pp. 180- 184 ,(2012) , 10.1002/AOC.2834
YOSHISUKE TSUDA, TETSUJI NUNOZAWA, KIMIHIRO YOSHIMOTO, Highly Stereoselective Grignard Reaction of an Aldopyranose : A Simple synthesis of 6-Deoxy-D-idose from D-Xylose Chemical & Pharmaceutical Bulletin. ,vol. 28, pp. 3223- 3231 ,(1980) , 10.1248/CPB.28.3223
Ugo Azzena, Giovanna Dettori, Maria Vittoria Idini, Luisa Pisano, Grazia Sechi, Regioselective reductive demethoxylation of 3,4,5-trimethoxystilbenes Tetrahedron. ,vol. 59, pp. 7961- 7966 ,(2003) , 10.1016/J.TET.2003.08.009
Ugo Azzena, Giovanna Dettori, Ilaria Mascia, Luisa Pisano, Mario Pittalis, Ion pairing effects on the regioselectivity of arylic versus benzylic C–O bond reductive cleavage: synthetic applications Tetrahedron. ,vol. 63, pp. 11998- 12006 ,(2007) , 10.1016/J.TET.2007.09.010
Catherine Kuehm-Caubère, Agnès Guilmart, Sandrine Adach-Becker, Yves Fort, Paul Caubère, DRAMATIC ACCELERATION OF THE DESULFURIZATION, WITH NI CONTAINING COMPLEX REDUCING AGENTS (NICRA'S) Tetrahedron Letters. ,vol. 39, pp. 8987- 8990 ,(1998) , 10.1016/S0040-4039(98)02034-6
Jorge Torres-Nieto, Juventino J. García, Catalytic desulfurization of dibenzothiophene using nickel supported on cross-linked polystyrene-PPh3 catalysts Journal of Organometallic Chemistry. ,vol. 694, pp. 780- 784 ,(2009) , 10.1016/J.JORGANCHEM.2008.12.019
Alberto Oviedo, Jorge Torres-Nieto, Alma Arévalo, Juventino J. García, Deoxydesulfurization of sulfones derived from dibenzothiophene using nickel compounds Journal of Molecular Catalysis A-chemical. ,vol. 293, pp. 65- 71 ,(2008) , 10.1016/J.MOLCATA.2008.06.015
Eugen Mülle, Gert Röscheisen, Das reaktive Verhalten von Tetraphenyläthandinatrium gegenüber aromatischen Halogenverbindungen Chemische Berichte. ,vol. 91, pp. 1106- 1114 ,(1958) , 10.1002/CBER.19580910538
Ugo Azzena, Mario Pittalis, Electron-transfer-induced reductive cleavage of chlorinated aryloxyalkanoic acids Tetrahedron. ,vol. 67, pp. 3360- 3362 ,(2011) , 10.1016/J.TET.2011.03.057