Relevant bibliographies by topics / Hydrothiolation

Academic literature on the topic 'Hydrothiolation'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Hydrothiolation"

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Rajesh, Nimmakuri, and Dipak Prajapati. "Indium(iii) catalysed regio- and stereoselective hydrothiolation of bromoalkynes." RSC Adv. 4, no. 61 (2014): 32108–12. http://dx.doi.org/10.1039/c4ra04359f.

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Hydrothiolation of bromoalkynes has been reported for the first time under metal catalysed conditions. Indium(iii) trifluoromethanesulfonate was demonstrated as the first catalyst which can catalyse the hydrothiolation of bromoalkynes with absolute regio- and stereoselectivity to generate synthetically valuable (Z)-β-bromo vinyl sulfides in good yields.
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2

Eremin, Dmitry B., Daniil A. Boiko, Eugenia V. Borkovskaya, Victor N. Khrustalev, Victor M. Chernyshev, and Valentine P. Ananikov. "Ten-fold boost of catalytic performance in thiol–yne click reaction enabled by a palladium diketonate complex with a hexafluoroacetylacetonate ligand." Catalysis Science & Technology 8, no. 12 (2018): 3073–80. http://dx.doi.org/10.1039/c8cy00173a.

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Brun, Elodie, Ke-Feng Zhang, Laure Guénée, and Jérôme Lacour. "Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives." Organic & Biomolecular Chemistry 18, no. 2 (2020): 250–54. http://dx.doi.org/10.1039/c9ob02375e.

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Palacios, Laura, Andrea Di Giuseppe, María José Artigas, Victor Polo, Fernando J. Lahoz, Ricardo Castarlenas, Jesús J. Pérez-Torrente, and Luis A. Oro. "Mechanistic insight into the pyridine enhanced α-selectivity in alkyne hydrothiolation catalysed by quinolinolate–rhodium(i)–N-heterocyclic carbene complexes." Catalysis Science & Technology 6, no. 24 (2016): 8548–61. http://dx.doi.org/10.1039/c6cy01884j.

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Yang, Xiao-Hui, Ryan T. Davison, Shao-Zhen Nie, Faben A. Cruz, Tristan M. McGinnis, and Vy M. Dong. "Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity." Journal of the American Chemical Society 141, no. 7 (February 8, 2019): 3006–13. http://dx.doi.org/10.1021/jacs.8b11395.

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Bruckchem Peixoto, Maura L., Isadora S. Lermen, Fabiane Gritzenco, Benhur Godoi, Carlos E. Bencke, and Marcelo Godoi. "Green hydrothiolation of dialkyl azodicarboxylates." Environmental Chemistry Letters 18, no. 3 (March 17, 2020): 967–73. http://dx.doi.org/10.1007/s10311-020-00980-4.

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Zhang, XingHui, and KeTai Wang. "Theoretical investigation of the mechanism of gold(i)-catalyzed hydrothiolation of alkynes and alkenes with phenthiol." RSC Adv. 5, no. 43 (2015): 34439–46. http://dx.doi.org/10.1039/c5ra01883h.

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Shard, Amit, Rajesh Kumar, Saima Saima, Nidhi Sharma, and Arun K. Sinha. "Amino acid and water-driven tunable green protocol to access S–S/C–S bonds via aerobic oxidative coupling and hydrothiolation." RSC Adv. 4, no. 63 (2014): 33399–407. http://dx.doi.org/10.1039/c4ra02909g.

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Yang, Yong, and Robert M. Rioux. "Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex." Green Chem. 16, no. 8 (2014): 3916–25. http://dx.doi.org/10.1039/c4gc00642a.

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Nakajima, Hana, Yuki Hazama, Yuki Sakata, Keisuke Uchida, Takamitsu Hosoya, and Suguru Yoshida. "Diverse diaryl sulfide synthesis through consecutive aryne reactions." Chemical Communications 57, no. 21 (2021): 2621–24. http://dx.doi.org/10.1039/d0cc08373a.

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Dissertations / Theses on the topic "Hydrothiolation"

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Wathier, Matthew James. "Mechanistic investigations of rhodium-catalyzed alkyne hydrothiolation." Thesis, University of British Columbia, 2016. http://hdl.handle.net/2429/59308.

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Herein, thorough mechanistic investigations into alkyne hydrothiolation catalyzed by [Tp*RhI(PPh₃)₂] (Tp* = tris(3,5-dimethylpyrazolyl)borate) are reported. The mechanism is shown to proceed through an intermediate [Tp*RhIIIH(SR)] complex (R = alkyl, aryl). Alkyne migratory insertion is shown to occur chemoselectively into the Rh-SR bond, despite the availability of a Rh-H bond, to produce a rhodathiacyclobutene intermediate. The regioselectivity of product formation is revealed to be the result of a competition between 1,2 and 2,1 migratory insertion of the alkyne to produce regioisomeric rhodathiacyclobutene intermediates. Product formation occurs upon reductive elimination, which is associatively induced by coordination of thiol. Putative off-cycle intermediates [Tp*RhH(SR)(PMe₃)] (R = alkyl, aryl) have been successfully synthesized from [Tp*RhH(CH₃)(PMe₃)]. The mechanism of formation of the [Tp*RhH(SR)(PMe₃)] complexes is proposed to involve the reductive elimination of methane, associatively induced by coordination of thiol. This mechanism is analogous to the mechanism proposed for alkyne hydrothiolation catalyzed by [Tp*Rh(PPh₃)₂]. Alkyne hydrothiolation reactions in the presence of [Tp*RhH(SR)(PMe₃)] are shown to produce the same product regioisomer as reactions catalyzed by [Tp*Rh(PPh₃)₂]. The synthesis of the vinyl sulfone-containing drug K777, currently in clinical trials for the treatment of Chagas disease, via alkyne hydrothiolation methodology catalyzed by [RhCl(PPh₃)₃], is reviewed. The methodology proves to be versatile in the synthesis of K777 and related analogues. The analogues are assessed in terms of their reactivity towards Michael addition as a method of predicting pharmacodynamics properties. The methanolic pKAs of a series of para-substituted aryl thiols are reported and correlated to their predicted aqueous pKA values. The Hammett dual parameter correlation to the experimental data reveals that the acidity constants are more dependent on the inductive effects of the para-substituent compared to the resonance effect. The dual parameter correlation also allows for the prediction of the methanolic and aqueous acidity constant of any para-substituted aryl thiol, as long as the substituent’s resonance and induction Hammett constants are known.
Science, Faculty of
Graduate
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2

Georgiev, David Georgiev. "Selective modification of biomolecules using radical mediated hydrothiolation chemistry." Thesis, University of Edinburgh, 2018. http://hdl.handle.net/1842/31322.

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Intracellular protein-protein interactions (PPIs) play a vital role in many biological processes. Although they are viewed as of high biological interest they prove difficult to explore as potential targets for drug discovery. Numerous studies have shown α- helical peptides 'locked' in their respective bioactive structure can greatly increase their performance by increasing their target affinity, resistance to proteolysis as well as facilitating cellular uptake. A striking feature of literature to date is how few studies utilise different stapling techniques when developing inhibitors for PPIs. Current methods generally exploit ruthenium catalysed ring closing metathesis (RCM) or copper catalysed alkyne/azide click (CuAAC) chemistry to generate geometrically constrained peptides. Even though these methods have shown great potential they both share a fundamental limitation as the chemistry can only be employed on small synthetic peptides and cannot be extended to larger proteins. Thiol-ene coupling (TEC) chemistry (Chapter 1) which is often described as a 'click' reaction due to its fast reaction rates, high yields, wide functional group tolerance and insensitivity to ambient oxygen and water has the potential to solve this challenge. Thiol-ene chemistry was investigated as an alternative stapling strategy by employing the naturally occurring amino acid L-cysteine (Cys) as a source of the thiyl radical and L-homoallylglycine (Hag), a non-natural amino acid shown to act as a methionine surrogate in protein synthesis to act as a source of an alkene functionality to form a potentially expressible thioether tether in Chapter 2. However, due to unsatisfactory results from the intramolecular thiol-ene cyclisation at the molar concentrations required for peptide or protein modification, and a promising new lead, the closely related thiol-yne reaction was investigated as an alternative in Chapter 3. Using a small library of peptides (14 mers) derived from α-Synuclein (αSyn), a protein mainly found in the presynaptic terminals in the brain and is believed to be key to the pathological progress of Parkinson's disease, a successful macrocyclisation was achieved between the side chains of cysteine (Cys) and homopropargylglycine (Hpg). Although the vinyl-thioether tether did not confer any helical conformation on the stapled peptides, the results clearly demonstrate a potential route for the development of expressible staples. Electron paramagnetic resonance (EPR) spectroscopy in combination with site-directed spin labelling (SDSL) of biomolecules has become a powerful tool for studying the structure and conformational dynamics of biomolecules. Typically, proteins are modified in a site-specific manner by utilising the side chains of cysteine residues to form disulphide bonds with spin active compounds, however, this strategy has its limitations. In Chapter 3 thiol-ene chemistry was investigated as an alternative biorthogonal method to spin label proteins and peptides. The newly synthesised sulfhydryl bearing nitroxide spin label was found to degrade upon exposure to radical promoting conditions, however, an alternative strategy was explored using more classical thiol-Michael chemistry to spin label dehydroalanine (Dha) modified peptides giving the desired spin labelled complex.
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Sabarre, Anthony. "Strategies towards carbon-carbon bond formation via tandem hydrothiolation/Kumada cross-coupling." Thesis, University of British Columbia, 2008. http://hdl.handle.net/2429/5327.

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Using recently developed methodology from our group, a variety of aryl and aliphatic terminal alkynes were reacted with n-propanethiol to undergo catalytic alkyne hydrothiolation in the presence Tp*Rh(PPh₃)₂ The alkynes examined afforded the branched isomer with high regioselectivity and moderate-to-high yield. Unsubstituted aryl alkynes, or those containing an electron-donating substituent at the para position, gave the branched vinyl sulfide in good isolated yield. In contrast, vinyl sulfides derived from aryl alkynes containing an electron-withdrawing substituent at the para position showed a decrease in reactivity and yield. The aliphatic alkynes that were investigated gave the desired branched vinyl sulfide in good yield. The isolated vinyl sulfides were then subjected to Kumada cross-coupling in the presence of NiCl₂(PPh₃)₂ with various aryl and aliphatic Grignard reagents, affording the corresponding 1,1 -disubstituted olefins. While benzyl-, phenyl- and trimethylsilylmagnesium halides were shown to be suitable cross-coupling partners, phenylethynyl-, vinyl- and n-butylmagnesium halides were not. Once the viability for the Kumada cross-coupling of vinyl sulfides was established, a one-pot protocol was investigated. It was shown that the one-pot procedure afforded the desired 1,1 -disubstituted olefin from readily available terminal alkynes in similar, and in some cases superior, yields than the two-step process.
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4

Fraser, Lauren Rae. "Structural characterization and catalytic activity of rhodium pyrazolylborate complexes in alkyne hydrothiolation." Thesis, University of British Columbia, 2007. http://hdl.handle.net/2429/31686.

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A series of hydrobis- and hydrotris(pyrazolyl)borate bis(triphenylphosphine) rhodium (I) complexes were synthesized and structurally characterized. These complexes are of the general form [BpRRh(PPh₃)₂] {BpR = H₂BR'₂ , R' = 3,5-dimethylpyrazolyl (2), pyrazolyl (3)}, and [TpRRh(PPh₃)₂] {TpR = HBR'₃ , R' = 3,5-dimethylpyrazolyl (1), pyrazolyl (4), 3-methylpyrazolyl (5), 3-phenylpyrazolyl (6), or 3-phenyl-5-methylpyrazolyl (7)}. Wilkinson's catalyst, [ClRh(PPh₃)₃], and the corresponding potassium salt of the ligands were mixed together in THF or toluene to produce known complexes 1-4 and new complexes 5-7. Both solid state and solution phase characterization were carried out for these complexes. The X-ray crystal structures were obtained for complexes 2, 4 and 5-7. All showed approximate square planar geometry with coordination of two pyrazolyl rings. IR spectroscopy (KBr pellet) was performed on complexes 1, 2 and 4-7 and the BH stretching frequencies were in the range of κ²-coordination. ¹H and ³¹P{¹H} NMR spectroscopy was performed on all seven complexes and variable temperature NMR spectroscopy for complexes 1 and 4-7 to examine the solution phase structures of these complexes. Complexes 1-7 were then used in alkyne hydrothiolation reactions with alkyl thiols as catalysts and their activities were examined. It was found that tris(pyrazolyl)borate complexes were superior to bis(pyrazolyl)borate complexes. As well, tris(pyrazolyl)borate rhodium complexes with substitution at the 3- and 5-positions on the pyrazolyl rings gave the best selectivity and yields, favoring the branched alkyl vinyl sulfides. Thus, complexes 1 and 7 have shown to be effective catalysts in alkyne hydrothiolation when using alkyl thiols to give regioselectively the branched isomer. A general method to produce branched alkyl vinyl sulfides has been discovered and will be presented in the body of this thesis.
Science, Faculty of
Chemistry, Department of
Graduate
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5

Shoai, Shiva. "Regioselective rhodium-catalyzed alkyne hydrothiolation with alkane thiols : substrate scope and mechanistic investigations." Thesis, University of British Columbia, 2010. http://hdl.handle.net/2429/27028.

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The optimization and substrate scope of ClRh(PPh₃)₃-catalyzed alkyne hydrothiolation with alkane thiols producing E-linear vinyl sulfides is presented. The reactions generally proceed in good yields with good selectivities for a variety of alkane thiols and alkynes. Bulky aliphatic alkynes result in the best selectivity, while aryl alkynes with para-substituted electron donating groups give the best yields. The presence of coordinating functional groups in either the substrate or solvent negatively affects the reaction both in yield and selectivity. Deuterium-labeling studies indicate that the reaction proceeds via thiol oxidative addition, migratory alkyne insertion into the Rh-H bond, followed by reductive elimination. Investigations into the mechanism of Tp*Rh(PPh₃)₂-catalyzed alkyne hydrothiolation are discussed. Five mechanisms are identified as being the most likely for this process; experiments were designed to support or refute each of these possibilities. Two mechanisms are definitively dismissed and another is dismissed as highly unlikely. The results cannot distinguish between the remaining two. The product distribution of hydrothiolation is analyzed and compared to other precatalysts. Stoichiometric reactivity of Tp*Rh(PPh₃)₂ with benzyl thiol is presented. Two new complexes, proposed to be Tp*Rh(PPh₃)₂(HSBn) and Tp*Rh(H)(SBn)(PPh₃), are generated. Presumed Tp*Rh(H)(SBn)(PPh₃), prepared in situ, does not catalyze alkyne hydrothiolation. Kinetic analysis was complicated by reaction inhibition at high thiol concentrations and competing side-reactions at high alkyne concentrations. Kinetic isotope effect experiments indicate that the alkyne is not involved in the rate-determining step; however, differences in the reactivity of several para-substituted phenyl acetylenes suggest that the rate-determining step is influenced by alkyne electronics. Overall, the reaction appears to obey the following rate law under normal catalytic reaction conditions rate = k[Tp*Rh(PPh₃)₂]¹[thiol]¹[alkyne]⁰. The reaction is hypothesized to proceed by thiol oxidative addition, migratory alkyne insertion into the Rh-S bond, followed by reductive elimination.
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Yang, Jun. "Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation : scope and limitations." Thesis, University of British Columbia, 2008. http://hdl.handle.net/2429/5534.

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Tp*Rh(PPh₃)₂ is a useful catalyst for alkyne hydrothiolation. Vinyl sulfides, the products of this reaction, are useful synthetic intermediates. The goal of this thesis project was to explore the scope and limitations of alkyne hydrothiolation with alkyl thiols catalyzed by Tp*Rh(PPh₃)₂ A variety of thiols and alkynes successfully undergo catalytic hydrothiolation. In general, the branched isomer was formed in good-to-excellent yields and with high selectivity. Electron rich phenylacetylenes were more reactive than electron deficient ones, and provided higher yields. Aliphatic alkynes need longer reaction times than aromatic alkynes in order to reach complete conversion. A broad range of functional groups were well tolerated, including halides, amines, nitriles, amines, ethers, esters and silanes. Alkoxy groups with the ability to coordinate with rhodium slowed down the catalytic turnover and lowered the yields. Strongly coordinating groups, such as pyridine, precluded catalysis. Alkynes that are Michael acceptors react with reversed regioselectivity. Hydrothiolation using internal alkynes was successful, although the reaction times were longer and temperatures are higher than that needed for terminal alkynes. Overall, the work presented in this thesis provides a general method in construction of branched alkyl vinyl sulfides from alkynes.
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7

Kiemele, Erica Rose. "Application of rhodium-catalyzed alkyne hydrothiolation to the syntheses of K777 and analogues : potential therapeutics for the treatment of Chagas' disease." Thesis, University of British Columbia, 2012. http://hdl.handle.net/2429/42600.

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8

Vuong, Khuong Quoc Chemistry Faculty of Science UNSW. "Metal complex catalysed C-X (X = S, O and N) bond formation." Awarded by:University of New South Wales. Chemistry, 2006. http://handle.unsw.edu.au/1959.4/23015.

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This thesis describes the catalysed addition of X-H bonds (X = S, O and N) to alkynes using a range of novel rhodium(I) and iridium(I) complexes containing hybrid bidentate phosphine-pyrazolyl, phosphine-imidazolyl and phosphine-N heterocyclic carbene (NHC) donor ligands. The synthesis of novel bidentate phosphine-pyrazolyl, phosphine-imidazolyl (P-N) and phosphine-NHC (PC) donor ligands and their cationic and neutral rhodium(I) and iridium(I) complexes [M(P N)(COD)]BPh4, [M(PC)(COD)]BPh4, [Ir(P-N)(CO)2]BPh4 and [M(P-N)(CO)Cl] were successfully performed. An unusual five coordinate iridium complex with phosphine-NHC ligands [Ir(PC)(COD)(CO)]BPh4 was also obtained. Seventeen single crystal X-ray structures of these new complexes were determined. A range of these novel rhodium and iridium complexes were effective as catalysts for the addition of thiophenol to a variety of alkynes. Iridium complexes were more effective than rhodium analogues. Cationic complexes were more effective than neutral complexes. Complexes with hybrid phosphine-nitrogen donor were more effective than complexes containing bidentate nitrogen donor ligands. An atom-economical, efficient method for the synthesis of cyclic acetals and bicyclic O,O-acetals was successfully developed based on the catalysed hydroalkoxylation. Readily prepared terminal and non-terminal alkyne diols were cyclised into bicyclic O,O-acetals in quantitative conversions in most cases. The efficiency of a range of rhodium and iridium complexes containing bidentate P-N and PC donor ligands as catalysts for the cyclisation of 4-pentyn-1-amine to 2-methyl-1-pyrroline varied significantly. The cationic iridium complexes with the bidentate phosphine-pyrazolyl ligands, [Ir(R2PyP)(COD)]BPh4 (2.39-2.42) were extremely efficient as catalysts for this transformation. Increasing the size of the substituent on or adjacent to the donor led to improvement in catalytic activity of the corresponding metal complexes. The mechanism of the catalysed hydroalkoxylation was proposed to proceed by the initial activation of the alkyne via ?? coordination to the metal centre. The ?? binding of both aliphatic and aromatic alkynes to [Ir(PyP)(CO)2]BPh4 (2.44) was observed by low temperature NMR and no reaction between 2.44 and alcohols was observed. In contrast, the facility in which thiol and amine oxidatively added to 2.44 led the proposal that in the hydrothiolation and hydroamination reaction, the catalytic cycle commences with the activation of the X-H bond (X = S, N) by an oxidative addition process.
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Book chapters on the topic "Hydrothiolation"

1

Kaufmann, D. E., and N. cal. "Hydrostannation, Hydrophosphination, and Hydrothiolation." In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00601.

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2

"1.4.6 Hydrothiolation, Hydroalkoxylation, and Hydroaryloxylation." In N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1, edited by Nolan and Cazin. Stuttgart: Georg Thieme Verlag, 2018. http://dx.doi.org/10.1055/sos-sd-223-00199.

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Eszenyi, Dániel, László Lázár, Anikó Borbás, and Ruairi O. McCourt. "Thiodisaccharides by Photoinduced Hydrothiolation of 2-Acetoxy Glycals." In Carbohydrate Chemistry, 33–43. CRC Press, 2017. http://dx.doi.org/10.1201/9781315120300-5.

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