77461-36-0Relevant academic research and scientific papers
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.
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.
Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues
Reich, Hans J.,Willis, William W.,Clark, Peter D.
, p. 2775 - 2784 (2007/10/02)
A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.
