40588-95-2Relevant articles and documents
Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion
Ananikov, Valentine P.,Burykina, Julia V.,Gordeev, Evgeniy G.,K?nig, Burkhard,Shlapakov, Nikita S.
, p. 10061 - 10070 (2020/10/13)
An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products-four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. This journal is
Hollow nanoshell-sphere Fe@Fe/Pd reactors: a magnetically recoverable catalyst for the Csp–S cross-coupling reactions in water
Abadi, Parvaneh Ghaderi-Shekhi,Rafiee, Ezzat,Joshaghani, Mohammad
, p. 1513 - 1525 (2018/06/21)
The hollow Pd–PVP–Fe nanosphere and Fe–PVP nanoparticle catalysts were synthesized by thermal method. Mixing of two metallic nanocatalysts was applied in the Csp–S cross-coupling reactions between diphenyl disulfide and phenylacetylene under mi
Reductive addition of the benzenethiyl radical to alkynes by amine-mediated single electron transfer reaction to diphenyl disulfide
Taniguchi, Tsuyoshi,Fujii, Tatsuya,Ldota, Atsushi,Lshibashi, Hiroyuki
supporting information; experimental part, p. 3298 - 3301 (2009/12/01)
Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compound
Reaction of Diphenyl Disulfide with Alkynes Promoted by Di-tert-butyl and Dibenzoyl Peroxides: a Useful Syntheic Route to 3- (and 2,3) Substituted Benzothiophenes
Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 1659 - 1664 (2007/10/02)
Thermal reactions of diphenyl disulfide 1 with phenylacetylenes 2a-e promoted by di-tert-butyl peroxide (TBP) at 110 or 150 deg C provides a useful synthetic route to the (2-substituted) 3-phenylbenzothiophenes 4a-e, which result from intramolecular cyclization of 1-phenyl-2-(phenylthio)vinyl radical intermediates 3a-e.Similar reactions of the disulfide 1 with tert-butyl- and trimethylsilylacetylenes 2f and 2g also provide the corresponding benzothiophenes 4f and 4g in satisfactory yields; low yields of the benzothiophene products 4h, i, however, are obtained with hex-1-yne 1h and hex-3-yne 1i.Evidence is presented that the thermal reaction of the disulfide 1 with the alkynes 2 at 100 deg C in the presence of dibenzoyl peroxide, while being of little use for the synthesis of benzothiophenes 4, generally leads to the 2-(phenylthio)vinyl benzoates 10; this is ascribed to initial addition of benzoyloxy radicals to alkyne triple bonds.
Free-Radical Reactions of Benzenethiol and Diphenyl Disulphide with Alkynes. Chemical Reactivity of Intermediate 2-(Phenylthio)vinyl Radicals
Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 2103 - 2109 (2007/10/02)
Reaction of benzenethiol at 100 deg C with neat alkyl- and dialkyl-acetylenes leads to virtually quantitative formation of isomeric mixtures of (E)- and (Z)-vinyl sulphide adducts in ratios which depend largely upon both the extent and the nature of alkyl substitution.Results are explained in terms of rapidly interconverting sp2-hybridized (E)- and (Z)-1-alkyl-2-(phenylthio)vinyl radical intermediates which can undergo hydrogen transfer from benzenethiol to an extent which is essentially dependent upon the steric hindrance of their cis-2-substituent.Consistent results are provided by related radical reactions of diphenyl disulphide with alkyl-substituted alkynes to afford varying amounts of 1,2-bis(phenylthio)ethylene adducts ascribable to SH2 reaction of the resulting 1-alkyl-2-(phenylthio)vinyl radicals with the disulphide present.Under analogous conditions benzenethiol and diphenyl disulphide react with phenylacetylenes to give vinyl sulphide or bissulphide adducts in a trans-stereoselective fashio.The findings are interpreted by suggesting, for the intermediate sp-hybridized 1-phenyl-2-(phenylthio)vinyl radicals, the occurrence of significant bonding interaction between the unpaired electron and the adjacent sulphur, which would essentially prevent attack of radical scavenger on the side cis to PhS.Evidence is also presented that 1-phenyl-2-(phenylthio)vinyl radicals can exhibit homolytic intramolecular cyclization reactions, leading to benzothiophene products to a comparatively much greater extent than the 1-alkyl-2-substituted analogues; however, 1-tert-butyl-2-(phenylthio)vinyl radical would represent a special case.
Boron Trifluoride-promoted Reaction of 4'-Nitrobenzenesulphenanilide and Its N-Methyl Derivative with Alkynes
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 1050 - 1052 (2007/10/02)
4'-Nitrobenzenesulphenanilide and its N-methyl derivative react with alkynes in the presence of boron trifluoride-diethyl ether presumably affording thiirenium ion intermediates, which are trapped by acetonitrile to give eventually β-acetamidinovinyl sulphides.
