77461-71-3Relevant articles and documents
Pd-NHC Catalytic System for the Efficient Atom-Economic Synthesis of Vinyl Sulfides from Tertiary, Secondary, or Primary Thiols
Degtyareva, Evgeniya S.,Burykina, Julia V.,Fakhrutdinov, Artem N.,Gordeev, Evgeniy G.,Khrustalev, Victor N.,Ananikov, Valentine P.
, p. 7208 - 7213 (2015/12/11)
Vinyl sulfides represent an important class of compounds in organic chemistry and materials science. Atom-economic addition of thiols to the triple bond of alkynes provides an excellent opportunity for environmentally friendly processes. We have found tha
Exclusive selectivity in the one-pot formation of C-C and C-Se bonds involving Ni-catalyzed alkyne hydroselenation: Optimization of the synthetic procedure and a mechanistic study
Orlov, Nikolay V.,Chistyakov, Igor V.,Khemchyan, Levon L.,Ananikov, Valentine P.,Beletskaya, Irina P.,Starikova, Zoya A.
, p. 12111 - 12121 (2015/01/09)
A unique Ni-catalyzed transformation is reported for the one-pot highly selective synthesis of previously unknown monoseleno-substituted 1,3-dienes starting from easily available terminal alkynes and benzeneselenol. The combination of a readily available catalyst precursor, Ni(acac)2, and an appropriately tuned phosphine ligand, PPh2Cy, resulted in the exclusive assembly of the s-gauche diene skeleton via the selective formation of C-C and C-Se bonds. The unusual diene products were stable under regular experimental conditions, and the products maintained the s-gauche geometry both in the solid state and in solution, as confirmed by X-ray analysis and NMR spectroscopy. Thorough mechanistic studies using ESI-MS revealed the key Ni-containing species involved in the reaction.
Catalytic adaptive recognition of thiol (SH) and selenol (SeH) groups toward synthesis of functionalized vinyl monomers
Ananikov, Valentine P.,Orlov, Nikolay V.,Zalesskiy, Sergey S.,Beletskaya, Irina P.,Khrustalev, Victor N.,Morokuma, Keiji,Musaev, Djamaladdin G.
experimental part, p. 6637 - 6649 (2012/06/15)
An unprecedented sustainable procedure was developed to produce functionalized vinyl monomers H2C=C(R)(FG) starting from a mixture of sulfur and selenium compounds as a functional group donor (FG = S or Se). The reaction serves as a model for e
Cerium(III)-mediated efficient and steroselective hydrochalcogenation of terminal alkynes
Silveira, Claudio C.,Mendes, Samuel R.,Rosa, Daniel D.,Zeni, Gilson
experimental part, p. 4015 - 4021 (2010/03/24)
Vinylic chalcogenides were synthesized stereospecifically by hydrochalcogenation of propargylic amines or alcohols mediated by cerium(III) chloride. The products were obtained in good yields and with high regio- and stereoselectivities. Georg Thieme Verla
Hydroselenation of alkynes using NaBH4/BMIMBF4: easy access to vinyl selenides
Lenard?o, Eder J.,Dutra, Luiz G.,Saraiva, Maiara T.,Jacob, Raquel G.,Perin, Gelson
, p. 8011 - 8013 (2008/03/18)
A general and easy method for the synthesis of several vinyl selenides using NaBH4 and BMIMBF4 as a recyclable solvent is described. This efficient and improved method furnishes the corresponding vinyl chalcogenides preferentially wi
Addition of chalcogenolate anions to terminal alkynes using microwave and solvent-free conditions: Easy access to bis-organochalcogen alkenes
Perin, Gelson,Jacob, Raquel G.,Dutra, Luiz G.,De Azambuja, Francisco,Dos Santos, Greice F. F.,Lenard?o, Eder J.
, p. 935 - 938 (2007/10/03)
We present here the reaction of diphenyl dichalcogenides (Se and Te) with propargyl alcohols using alumina supported sodium borohydride under solvent-free conditions. This efficient and improved method is general and furnishes the corresponding vinyl chal
Indium(I) iodide-mediated chemio-, regio-, and stereoselective hydroselenation of 2-alkyn-1-ol derivatives
Do Rego Barros, Olga Soares,Lang, Ernesto Shulz,De Oliveira, Carlos Alberto Fernandes,Peppe, Clovis,Zeni, Gilson
, p. 7921 - 7923 (2007/10/03)
Indium(I) iodide efficiently promotes the chemio-, regio-, and stereoselective hydroselenation of 2-alkyn-1-ol derivatives with diphenyl diselenide to produce the Markovnikov adducts with stereochemistry corresponding to an anti addition of the selenol co
Regiospecific hydroselenation of terminal acetylenes using aluminum phenylselenolate anions
Dabdoub, Miguel J.,Cassol, Tania M.,Batista, Antonio C. F.
, p. 9005 - 9008 (2007/10/03)
Regiospecific hydroselenation of terminal acetylenes using aluminum phenylselenolates afforded the 1-organyl-1-phenylseleno ethenes in good yields. The first example of exclusive formation of the hydroselenation Markovnikov adducts is described. Copyright
The first example of transitionmetal-catalyzed hydroselenation of acetylenes
Kuniyasu, Hitoshi,Ogawa, Akiya,Sato, Ken-Ichiro,Ryu, Iihyong,Sonoda, Noboru
, p. 5525 - 5528 (2007/10/02)
A variety of transition metal complexes catalyzed the regioselective hydroselenation of acetylenes. In particular, the palladium acetate-catalyzed reaction afforded the Markovnikov adducts with high selectivity.
PREPARATION OF 3-HYDROXYL-VINYL SELENIDES AND 1,3-BIS(SELENO)-PROPENES
Renard, M.,Hevesi, L.
, p. 5939 - 5954 (2007/10/02)
Z and E 3-hydroxy-vinyl selenides can be prepared with very high stereoselectivity respectively by nucleophilic addition of selenolates to propargyl alcohols and by selenylation followed by LiAlH4 reduction of the same propargyl alcohols. 1,3-Bis(seleno)-
