185259-53-4Relevant articles and documents
A stereoselective route to (E)-vinylic selenides through the palladium-catalyzed cross-coupling reaction of selenovinylicdialkylboranes with alkyl halides
Yang, Yu,Huang, Xian
, p. 345 - 349 (1997)
The reaction of selenovinylicdialkylboranes with alkyl halides takes place readily in the presence of Pd(PPh3)4 and sodium methoxide to afford (E)-vinylic selenides in excellent yields.
Copper-Silver Dual Catalyzed Decyanative C–Se Cross-Coupling
Mukherjee, Nirmalya,Kundu, Debasish,Ranu, Brindaban C.
, p. 329 - 338 (2017/02/05)
Traditionally, a metal-catalyzed cross-coupling reaction is governed by displacement of leaving groups such as halogens, tosylates, etc. by different nucleophiles leading to the formation of carbon-carbon and carbon-heteroatom bonds. Besides displacement of traditional leaving groups in coupling reactions decyanative cross-coupling has also received current attention. The objective of this work is to develop a decyanative cross-coupling through metal-assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross-coupling of aryl selenocyanate with aryl-/alkylacetylenes, boronic acids and silanes has been accomplished by a copper-assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best yield of product was obtained using 5 mol% of Cu(OAc)2, Ag2CO3(20 mol%) and Cs2CO3(1 equiv.) at 100 °C for 8 h in N-methylpyrrolidinone (NMP). The advantages of simple operation, high yields and general applicability make this procedure more attractive. A mechanistic pathway has been proposed. Silver plays a key role in the decyanation process. A plausible mechanistic pathway of this decyanative carbon-selenium cross-coupling has been proposed based on UV, EPR, HR-MS and IR analytical data along with results obtained from control experiments. (Figure presented.).
Silver-catalyzed carbon-selenium cross-coupling using N-(phenylseleno)phthalimide: An alternate approach to the synthesis of organoselenides
Mukherjee, Nirmalya,Pal, Subhajit,Saha, Amit,Ranu, Brindaban C.
, p. 51 - 56 (2017/01/10)
Silver(I) catalyzed phenylselenylation of terminal alkynes and organoboronic acids has been demonstrated using N-(phenylseleno)phthalimide as an electrophilic SePh donor. A wide variety of terminal alkynes and organoboronic acids are selenylated efficiently to produce the corresponding alkynyl and diaryl selenides, respectively, in good yields. Silver(I) acts as a Lewis acid in this process.
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
Transition-metal free synthesis of diaryl vinyl selenides: A simple synthetic approach with high selectivity
Mohan, Balaji,Hwang, Sori,Woo, Hyunje,Park, Kang Hyun
, p. 2699 - 2702 (2014/04/17)
A simple, highly efficient synthetic protocol is developed for the synthesis of unsymmetrical diaryl vinyl selenides from diaryldiselenide and β-bromo styrene under transition-metal free conditions in N,N′-dimethyl propylene urea and 130 °C to afford high yields and excellent selectivities. This method provides a new strategy to fabricate a wide variety of important substituted molecular skeletons and an alternative to conventionally used metal salts, additives, and ligands.
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
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.
Lanthanum-catalyzed stereoselective synthesis of vinyl sulfides and selenides
Reddy, V. Prakash,Swapna,Kumar, A. Vijay,Rao, K. Rama
experimental part, p. 293 - 296 (2010/03/26)
Lanthanum oxide/TMEDA-catalyzed cross-coupling of vinyl halides with thiols/diphenyl diselenide in anhydrous DMSO and KOH is reported. Utilizing this protocol various vinyl sulfides and selenides were synthesized in excellent yields with retention of the stereochemistry. The catalyst was recyclable.
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 nano-catalyst: Sustainable phenyl-selenylation of aryl iodides and vinyl bromides in water under ligand free conditions
Saha, Amit,Saha, Debasree,Ranu, Brindaban C.
experimental part, p. 1652 - 1657 (2009/06/28)
A simple and efficient procedure for the synthesis of aryl- and vinyl-selenides has been developed by a copper nanoparticle catalysed reaction of aryl iodide/vinyl bromide with diphenyl diselenide in the presence of zinc in water. (E)-Vinyl bromides produce (E)-vinyl selenides stereoselectively, whereas (Z)-vinyl bromides provide mixtures of (E) and (Z) isomers. The catalyst was recycled.
