15436-06-3Relevant articles and documents
Nucleophilic Substitutions of Unactivated Vinyl Halides with Alkanethiolate Anions in Hexamethylphophoramide
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Montanucci, Manuela
, p. 4795 - 4800 (1983)
The reactions of unactivated vinyl halides with the sodium salts of alkanethiols in HMPA gave vinyl alkyl sufides in high yields.These reactions occur with complete retention of configuration.With di-, tri-, and tetrachloroethylenes all the chlorine atoms are substituted by alkylthio groups.By treatment with alkanethiolates the vinyl sulfides are dealkylated to give the sodium salts of the ene thiols.By reaction with sodium all the alkylthiogroups present in the molecule suffer fragmentation to give the sodium salts of the corresponding mercaptoethylenes.
[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO
Guo, Can-Cheng,Li, Hui,Liu, Qiang,Luo, Wei-Ping,Nie, Zhiwen,Su, Miao-Dong,Yang, Tonglin
, (2022/02/10)
A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.
A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
Czyz,Weragoda,Monaghan,Connell,Brzozowski,Scully,Burton,Lupton,Polyzos
supporting information, p. 1543 - 1551 (2018/03/08)
The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.
Cobalt modified N-doped carbon nanotubes for catalytic C=C bond formation via dehydrogenative coupling of benzyl alcohols and DMSO
Li, Jinlei,Liu, Guoliang,Shi, Lijun,Xing, Qi,Li, Fuwei
supporting information, p. 5782 - 5788 (2017/12/26)
The development of heterogeneous, cost-effective and environmentally benign catalysts to construct C=C bonds is highly desirable. We report here Co@N-doped carbon nanotubes (Co@NCNT) as a catalyst for a novel synthesis of styryl sulfides via dehydrogenative coupling of benzyl alcohols and DMSO under anaerobic conditions. This reaction maintains high atom efficiency as the C=C bond is formed without the cracking of the C-S bond. We proposed that Co modified N-doped carbon sites are the active sites, different from traditionally believed metal centers for dehydrogenative C-C coupling. Moreover, the Co@NCNT catalyst could be easily separated and recycled for at least six runs. This work opens up a new application of metal-N-C catalysts in C=C bond-forming reactions in synthetic chemistry.
Direct syntheses of styryl ethers from benzyl alcohols via ag nanoparticle-catalyzed tandem aerobic oxidation
Zhang, Qi,Cai, Shuangfei,Li, Linsen,Chen, Yifeng,Rong, Hongpan,Niu, Zhiqiang,Liu, Junjia,He, Wei,Li, Yadong
, p. 1681 - 1684 (2013/07/26)
Ag nanoparticle-catalyzed aerobic oxidation of benzyl alcohols in basic DMSO gave efficient formation of styryl ethers, featuring single carbon transfer and Ci - C and C-O bond formation. A deuterium labeling experiment established that DMSO was the carbo
One-pot synthesis of alkyl styryl sulfides free from transition metal/ligand catalyst and thiols
Heredia, Adrian A.,Penenory, Alicia B.
, p. 991 - 997 (2013/03/14)
A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols. Copyright
A Convenient Preparation of Chalcogenoenynes from β-Bromovinyl Ketene Chalcogenoacetals
Zeni, Gilson,Stracke, Marcelo Paulo,Lissner, Elizeo,Braga, Antonio Luiz
, p. 1880 - 1882 (2007/10/03)
β-Bromovinyl ketene chalcogenoacetals have been synthesized stereoselectively via electrophilic addition of the benzene-selenenyl bromide to substituted alkynes. The palladium-catalyzed cross-coupling reaction of β-bromovinyl ketene chalcogenoacetals with
Mg-promoted stereoselective desulfonation of β-arylvinyl sulfone derivatives
Nishiguchi, Ikuzo,Matsumoto, Takeshi,Kuwahara, Takeshi,Kyoda, Makoto,Maekawa, Hirofumi
, p. 478 - 479 (2007/10/03)
β-Arylvinyl ρ-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of ρ-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species followed by stereoselective elimination of a sulfonyl group.
Reaction of dimethyl sulfide ditriflate with alkenes. Synthesis of sulfur derivatives of nortricyclane
Nenajdenko, Valentine G.,Vertelezkij, Pavel V.,Gridnev, Ilya D.,Shevchenko, Nikolai E.,Balenkova, Elizabeth S.
, p. 8173 - 8180 (2007/10/03)
The reaction of dimethyl sulfide ditriflate with alkenes leads to the corresponding sulfonium salts. Dependence of the reaction course on the substrate structure is discussed. In the reactions with norbornene and norbornadiene the sulfonium salts with nortricyclene skeleton were obtained. The configurations of the two isomeric disubstituted nortricyclanes 21a,b were determined by NMR.
Selective synthesis of cis-α,β-unsaturated sulfoxides and sulfides by the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes
Kokin, Keisuke,Tsuboi, Shuji,Motoyoshiya, Jiro,Hayashi, Sadao
, p. 637 - 640 (2007/10/03)
cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.
