51256-41-8Relevant academic research and scientific papers
Indium(I) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium(0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Banerjee, Subhash
, p. 423 - 425 (2006)
Diphenyl diselenide (and disulfide) undergo facile reaction with indium(I) iodide and the corresponding intermediate complex condenses in situ with a variety of substituted vinyl bromides in the presence of a catalytic amount of tetrakis-(triphenylphosphine)palladium(O) [Pd(PPh3)4] in THF at room temperature to produce vinylic selenides and sulfides in good yields. The conversion of (E)-vinyl bromides is remarkably stereoselective giving (E)-Vinyl selenides (and sulpfides) whereas the stereoselectivity in reaction of (Z)-vinyl bromides is not very good.
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions
Castoldi, Laura,Di Tommaso, Ester Maria,Gr?fen, Barbara,Olofsson, Berit,Reitti, Marcus
supporting information, p. 15512 - 15516 (2020/06/23)
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites
Larin, Egor M.,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan
, p. 311 - 319 (2019/12/28)
A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
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
Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex
Yang, Yong,Rioux, Robert M.
, p. 3916 - 3925 (2014/08/05)
A practical, efficient, and low-cost heterogeneous catalyst consisting of a Cu-NHC (N-heterocyclic carbene) complex grafted to SBA-15 silica for the catalytic hydrothiolation of alkynes and electron-deficient alkenes under mild reaction conditions has been developed. The heterogeneous catalyst displays higher activity and stereoselectivity to Z-anti-Markovnikov isomers compared with the homogeneous analog under otherwise identical reaction conditions. The catalytic system is applicable to a broad range of alkynes and thiols and is recyclable without significant loss in catalytic performance. High activity and perfect selectivity to alkyl sulfides formed by the addition of electron-deficient alkenes to various thiols catalyzed by the supported Cu-NHC complex were also realized. This journal is the Partner Organisations 2014.
Stereoselective heck reactions with vinyl sulfoxides, sulfides and sulfones
Bachmann, Daniel G.,Wittwer, Christopher C.,Gillingham, Dennis G.
supporting information, p. 3703 - 3707 (2014/01/06)
We report the Heck cross-coupling of notoriously unreactive, but synthetically valuable olefins: vinyl sulfoxides, vinyl sulfones, and vinyl sulfides. Key findings include the importance of the sterically hindered (tri-tert-butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, E-selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry. Copyright
Glycerol/CuI/Zn as a recyclable catalytic system for synthesis of vinyl sulfides and tellurides
Gon?alves, Lóren C.C.,Lima, David B.,Borba, Pedro M.Y.,Perin, Gelson,Alves, Diego,Jacob, Raquel G.,Lenard?o, Eder J.
, p. 3475 - 3480 (2013/07/05)
A convenient approach to the Cu-catalyzed coupling of diphenyl disulfide and diphenyl ditelluride with vinyl bromides using a recyclable catalytic system and glycerol as a green solvent is described. This protocol was efficiently used in the preparation of vinyl sulfides and vinyl tellurides with a variety of substituents in good yields and stereoselectively. The solvent/catalyst system was directly reused for four cycles without loss of activity.
Ligand-controlled regioselectivity in the hydrothiolation of alkynes by rhodium N-heterocyclic carbene catalysts
Di Giuseppe, Andrea,Castarlenas, Ricardo,Perez-Torrente, Jesus J.,Crucianelli, Marcello,Polo, Victor,Sancho, Rodrigo,Lahoz, Fernando J.,Oro, Luis A.
scheme or table, p. 8171 - 8183 (2012/07/13)
Rh-N-heterocyclic carbene compounds [Rh(μ-Cl)(IPr)(ν2- olefin)]2 and RhCl(IPr)(py)(ν2-olefin) (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-carbene, py = pyridine, olefin = cyclooctene or ethylene) are highly active cata
Carbon dioxide mediated stereoselective copper-catalyzed reductive coupling of alkynes and thiols
Nurhanna Riduan, Siti,Ying, Jackie Y.,Zhang, Yugen
supporting information; experimental part, p. 1780 - 1783 (2012/06/04)
A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO2 atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step in determining the stereoselectivity, and an equivalent amount of water is found to play an active role as a proton donor.
