39984-84-4Relevant academic research and scientific papers
Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C?S Formation
Ang, Nate W. J.,Ackermann, Lutz
supporting information, p. 4883 - 4887 (2021/02/26)
Sulfur-containing molecules are of utmost topical importance towards the effective development of pharmaceuticals and functional materials. Herein, we present an efficient and mild electrochemical thiolation by cross-electrophile coupling of alkyl bromide
Synergetic Effect of Monomer Functional Group Coordination in Catalytic Insertion Polymerization
Leicht, Hannes,G?ttker-Schnetmann, Inigo,Mecking, Stefan
supporting information, p. 6823 - 6826 (2017/05/31)
PhS- and PhNH-functionalized dienes are copolymerized efficiently with butadiene to stereoregular copolymers by [(mesitylene)Ni(allyl)][BArF4] (Ni-1). Overall polymerization rates and comonomer incorporations depend strongly on the l
Synthesis of thioethers by ini3-catalyzed substitution of siloxy group using thiosilanes
Nishimoto, Yoshihiro,Okita, Aya,Baba, Akio,Yasuda, Makoto
, (2016/11/02)
The substitution of a siloxy group using thiosilanes smoothly occurred in the presence of InI3 catalyst to yield the corresponding thioethers. InI3was a specifically effective catalyst in this reaction system, while other typical Lew
Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
Pan, Xiangcheng,Curran, Dennis P.
supporting information, p. 2728 - 2731 (2014/06/09)
Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.
Synthesis of a wide range of thioethers by indium triiodide catalyzed direct coupling between alkyl acetates and thiosilanes
Nishimoto, Yoshihiro,Okita, Aya,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 1846 - 1849 (2012/06/18)
An indium triiodide-catalyzed substitution of the acetoxy group in alkyl acetates with thiosilanes provides access to a variety of thioethers. The method is efficient for a wide scope of acetates such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic acetates.
Sterically governed selectivity in palladium-assisted allylic alkylation
Kleimark, Jonatan,Johansson, Charlotte,Olsson, Susanne,Hakansson, Mikael,Hansson, Sverker,Akermark, Bjoern,Norrby, Per-Ola
experimental part, p. 230 - 238 (2011/03/17)
The selectivity in the Pd-assisted allylic alkylation has been investigated in a system with a ligand tethered to the allylic moiety. Isolation of (η3-allyl)Pd complexes and stoichiometric reaction with malonate nucleophiles allowed separation
Cyclization by intramolecular carbolithiation of alkyl- and vinyllithiums prepared by the action of aromatic radical anions on phenyl thioethers. High stereoselectivity in the cyclization accelerated by an allylic lithium oxyanion
Deng, Kai,Bensari-Bouguerra, Ahlem,Whetstone, Joseph,Cohen, Theodore
, p. 2360 - 2372 (2007/10/03)
The reductive lithiation of alkyl and vinyl phenyl thioethers by aromatic radical anions is shown to be the most general method yet known for preparing organolithiums capable of intramolecular carbometalation of unactivated alkenes to produce five-membered rings and in one case a four-membered ring (in a far higher yield than known cases). The relative rates of cyclization for alkyllithiums are secondary > tertiary > primary, and the yields are very high. In the secondary case, the stereoselectivity is extremely high, producing a cyclopentylmethyllithium with a trans-2-alkyl substituent. A remarkable finding is that for all of the organolithiums a lithium oxyanionic group in the proximal allylic position to the alkene greatly accelerates the cyclization and leads almost exclusively to a trans relationship between the CH2Li group and the OLi group, the opposite relationship from that observed in intramolecular carbolithiations by allyllithiums. A mechanistic rationale for this divergence is discussed. One of the two types of proximal homoallylic lithium oxyanions exerts an analogous effect. An intriguing limitation, even occurring with the highly reactive secondary organolithium and in the presence of an allylic oxyanionic group, is the failure of intramolecular carbolithiation when a methyl group is at the terminus of the alkene.
Generation and intramolecular cyclization of α-phenylsulfonyl and α-alkylsulfonyl radicals
Tsai, Yeun-Min,Chang, Fu-Chang,Huang, Jimin,Shiu, Chi-Lung,Kao, Chai-Lin,Liu, Jyh-Shiunn
, p. 4291 - 4308 (2007/10/03)
α-Phenylsulfonyl radicals are generated by the reaction of diphenyl dithioacetals or phenyl α-chlorosulfides with tributyltin hydride. Alkyl phenyl dithioacetals react selectively with tributyltin hydride to give α-alkylsulfonyl radicals. 5-Exo-type of intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The cis/trans ratio of the cyclized product varies according to the reaction rates. With a faster cyclization, cis-isomer is the major product. A slower cyclization gives more trans-product.
Expanding the versatility of Schwartz' reagent: Hydrozirconation of vinylic acid and acetylenic acyl silanes
Lipshutz,Lindsley,Bhandari
, p. 4669 - 4672 (2007/10/02)
By virtue of a triisopropylsilyl acyl silane contained with a substrate undergoing hydrozirconation, chemospecificity can be realized favoring addition across the alkene or alkyne, rather than competitive 1,2-addition of hydride to the carbonyl portion of
Hole transfer promoted hydrogenation: One-electron oxidation as a strategy for selective reduction of π-bonds
Mirafzal, Gholam A.,Liu, Jianping,Bauld, Nathan L.
, p. 6072 - 6077 (2007/10/02)
One-electron oxidation is developed as a strategy for selective and efficient reduction of relatively ionizable functionalities, including conjugated dienes, styrenes, vinyl sulfides, aromatics, and even strained σ-bonds. Reduction is highly sensitive to substrate ionizability and permits selective reduction of the more ionizable function in a difunctional context. Ionization of the substrates to cation radicals is effected via the mild hole transfer agent tris(4-bromophenyl)aminium hexachloroantimonate, and subsequent reduction of the cation radicals is accomplished by tributyltin hydride. The new reduction conditions provide a novel route for generating free radicals which may prove useful in the field of radical cyclizations. This is especially attractive in the case of phenyl vinyl sulfides since the phenylthio group, which remains intact subsequent to cyclization, provides versatile functionality for further synthetic operations.
