60466-30-0Relevant articles and documents
Preparation of (Z)- and (E)-vinyl selenides utilizing vinylboronic acids and vinylboronic esters in ionic liquids
Kabalka, George W.,Venkataiah, Bollu
, p. 3703 - 3705 (2002)
Vinylboronic acids and vinylboronic esters react with phenylselenyl chloride in ionic liquids to generate vinyl selenides stereospecifically.
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
Selenolation of Aryl Iodides and Bromides Enabled by a Bench-Stable PdI Dimer
Senol, Erdem,Scattolin, Thomas,Schoenebeck, Franziska
supporting information, p. 9419 - 9422 (2019/04/30)
The use of an air- and moisture-stable dinuclear PdI complex as an efficient catalyst for the formation of C(sp2)?SeR bonds is here reported. The privileged reactivity of the PdI dimer allows for the direct use of selenolates as nucleophiles in the cross-coupling. Although previous methodologies suffer from catalyst poisoning through the formation of Pd-ate complexes, the mechanistically distinct dinuclear PdI catalyst circumvents this challenge. A wide variety of aryl bromides and iodides were efficiently coupled under relatively mild reaction conditions with broad functional group tolerance. Mechanistic and computational data are presented in support of direct PdI reactivity.
1,1-Dibromoalkenes as versatile reagents to a transition metal-free and stereoselective synthesis of (E)-1-bromo-1-selenoalkenes and ketene selenoacetals
Webber, Rodrigo,Peglow, Thiago J.,Nobre, Patrick C.,Barcellos, Angelita M.,Roehrs, Juliano A.,Schumacher, Ricardo F.,Perin, Gelson
supporting information, p. 4128 - 4132 (2016/08/24)
We describe here a metal-free and selective method for the synthesis of (E)-1-bromo-1-seleno alkenes and ketene selenoacetals by a stoichiometric and temperature-controlled reaction. These protocols employ a diverse array of 1,1-dibromoalkenes and different diaryl diselenides to afford the corresponding products in good yields and in a short reaction time.
DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations
Lopes, Eric F.,Gon?alves, Lóren C.,Vinueza, Julio C.G.,Jacob, Raquel G.,Perin, Gelson,Santi, Claudio,Lenard?o, Eder J.
supporting information, p. 6890 - 6895 (2015/11/27)
We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl
A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations
Tidei, Caterina,Sancineto, Luca,Bagnoli, Luana,Battistelli, Benedetta,Marini, Francesca,Santi, Claudio
supporting information, p. 5968 - 5975 (2015/03/30)
Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste
Glycerol as a promoting medium for cross-coupling reactions of diaryl diselenides with vinyl bromides
Gonalves, Loren C.,Fiss, Gabriela F.,Perin, Gelson,Alves, Diego,Jacob, Raquel G.,Lenard?o, Eder J.
supporting information; experimental part, p. 6772 - 6775 (2011/02/24)
We described herein the use of glycerol as a novel solvent in the cross-coupling reaction of diaryl diselenides with vinyl bromides catalyzed by CuI. This cross-coupling reaction was performed with diaryl diselenides and (Z)- or (E)-vinyl bromides bearing electron-withdrawing and electron-donating groups, affording the corresponding vinyl selenides in good to excellent yields. The mixture glycerol/catalyst can be directly reused for further cross-coupling reactions.
Copper-catalyzed stereoselective synthesis of vinyl selenides under ligand-free conditions
Reddy, Vutukuri Prakash,Kumar, Akkilagunta Vijay,Rao, Kakulapati Rama
experimental part, p. 212 - 214 (2010/08/20)
A mild and efficient protocol for the stereoselective synthesis of vinyl selenides catalyzed by CuO nanoparticles as recyclable catalyst under ligand-free conditions is reported. This methodology results in the synthesis of a variety of vinyl selenides in excellent yields with retention of stereochemistry.
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
Cesium Salt-Catalyzed Addition of Diphenyl Dichalcogenides to Alkynes: Selective Synthesis of Bis- and Mono(phenylchalcogeno)alkenes
Nishiyama, Yutaka,Ohnishi, Haruko,Koguma, Yuya
experimental part, p. 1170 - 1174 (2009/12/25)
A cesium salt has a unique catalytic ability for the reaction of alkynes with diphenyl dichalcogenides. When the diphenyl dichalcogenides, such as the disulfide, diselenide, or ditelluride, were allowed to react with alkynes in the presence of a catalytic
