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Journal articles on the topic 'Hydrothiolation'

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

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1

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Lynch, Dylan M., and Eoin M. Scanlan. "Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates." Molecules 25, no. 13 (July 7, 2020): 3094. http://dx.doi.org/10.3390/molecules25133094.

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Sulfur centered radicals are widely employed in chemical synthesis, in particular for alkene and alkyne hydrothiolation towards thioether bioconjugates. The steadfast radical chain process that enables efficient hydrothiolation has been explored in the context of cascade reactions to furnish complex molecular architectures. The use of thiyl radicals offers a much cheaper and less toxic alternative to the archetypal organotin-based radical methods. This review outlines the development of thiyl radicals as reactive intermediates for initiating carbocyclization cascades. Key developments in cascade cyclization methodology are presented and applications for natural product synthesis are discussed. The review provides a chronological account of the field, beginning in the early seventies up to very recent examples; a span of almost 50 years.
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12

Bhadra, Sukalyan, and Brindaban C. Ranu. "Water-promoted regioselective hydrothiolation of alkynes." Canadian Journal of Chemistry 87, no. 11 (November 2009): 1605–9. http://dx.doi.org/10.1139/v09-130.

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Water promotes hydrothiolation of unactivated alkynes efficiently without any catalyst or additive. The reaction at room temperature furnishes vinyl sulfides with high regioselectivity via anti-Markovnikov addition. The terminal alkynes provide dithiolanes at 80 °C by bis-addition. The reactions are very clean and high yielding.
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13

Bege, Miklós, Ilona Bereczki, Mihály Herczeg, Máté Kicsák, Dániel Eszenyi, Pál Herczegh, and Anikó Borbás. "A low-temperature, photoinduced thiol–ene click reaction: a mild and efficient method for the synthesis of sugar-modified nucleosides." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9226–33. http://dx.doi.org/10.1039/c7ob02184d.

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While studying the radical mediated hydrothiolation of nucleoside enofuranosides, an unusual temperature effect was observed by the exploitation of which various thio-substituted nucleoside analogues were produced.
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14

Ziyaei Halimehjani, A., and B. Breit. "Catalyst-free hydrothiolation of alkynes with dithiocarbamic acids." Chemical Communications 55, no. 9 (2019): 1253–55. http://dx.doi.org/10.1039/c8cc09726g.

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A highly regio- and stereocontrolled procedure for the synthesis of vinyl dithiocarbamates via catalyst-free hydrothiolation of unactivated alkynes with in situ prepared dithiocarbamic acids with total atom economy is reported.
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15

Lázár, László, László Juhász, Gyula Batta, Anikó Borbás, and László Somsák. "Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals." New Journal of Chemistry 41, no. 3 (2017): 1284–92. http://dx.doi.org/10.1039/c6nj03751h.

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Unique thiodisaccharides of β-manno type featuring C-glycosylic structure with an anomeric functional group for further elaboration were obtained by radical-mediated hydrothiolation of 1-C-acceptor-substituted glycals.
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16

Kondoh, Azusa, Hideki Yorimitsu, and Koichiro Oshima. "Palladium-Catalyzedanti-Hydrothiolation of 1-Alkynylphosphines." Organic Letters 9, no. 7 (March 2007): 1383–85. http://dx.doi.org/10.1021/ol0702876.

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17

Cabrero-Antonino, Jose R., Antonio Leyva-Pérez, and Avelino Corma. "Iron-Catalysed Markovnikov Hydrothiolation of Styrenes." Advanced Synthesis & Catalysis 354, no. 4 (February 23, 2012): 678–87. http://dx.doi.org/10.1002/adsc.201100731.

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18

Mosaferi, Eliar, David Ripsman, and Douglas W. Stephan. "The air-stable carbocation salt [(MeOC6H4)CPh2][BF4] in Lewis acid catalyzed hydrothiolation of alkenes." Chemical Communications 52, no. 53 (2016): 8291–93. http://dx.doi.org/10.1039/c6cc03970g.

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Markovnikov hydrothiolation of 1,1-disubstituted and trisubstituted olefins (20 examples) is catalyzed by Lewis acids, including the air-stable trityl-cation salt [(MeOC6H4)CPh2][BF4] 3.
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19

Kleinhans, George, Gregorio Guisado-Barrios, David C. Liles, Guy Bertrand, and Daniela I. Bezuidenhout. "A rhodium(i)–oxygen adduct as a selective catalyst for one-pot sequential alkyne dimerization-hydrothiolation tandem reactions." Chemical Communications 52, no. 17 (2016): 3504–7. http://dx.doi.org/10.1039/c6cc00029k.

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An air-stable rhodium(i)–oxygen adduct featuring a CNC-pincer ligand, based on 1,2,3-triazol-5-ylidenes, catalyzes the homo-dimerization and hydrothiolation of alkynes, affording the gem-enyne and α-vinyl sulfide isomers, respectively, with excellent selectivity.
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20

Kathe, Prasad M., and Ivana Fleischer. "Palladium-Catalyzed Tandem Isomerization/Hydrothiolation of Allylarenes." Organic Letters 21, no. 7 (March 14, 2019): 2213–17. http://dx.doi.org/10.1021/acs.orglett.9b00504.

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21

Menggenbateer, Meda Narsireddy, Giovanni Ferrara, Naoko Nishina, Tienan Jin, and Yoshinori Yamamoto. "Gold-catalyzed regiospecific intermolecular hydrothiolation of allenes." Tetrahedron Letters 51, no. 35 (September 2010): 4627–29. http://dx.doi.org/10.1016/j.tetlet.2010.06.125.

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22

McCourt, Ruairí O., and Eoin M. Scanlan. "Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes." Chemistry – A European Journal 26, no. 68 (October 23, 2020): 15804–10. http://dx.doi.org/10.1002/chem.202002542.

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23

He, Chuan, Chad Brouwer, and Ronald Rahaman. "Gold(I)-Mediated Hydrothiolation of Conjugated Olefins." Synlett 2007, no. 11 (July 2007): 1785–89. http://dx.doi.org/10.1055/s-2007-984519.

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24

Nie, Shaozhen, Alexander Lu, Erin L. Kuker, and Vy M. Dong. "Enantioselective Hydrothiolation: Diverging Cyclopropenes through Ligand Control." Journal of the American Chemical Society 143, no. 16 (April 15, 2021): 6176–84. http://dx.doi.org/10.1021/jacs.1c00939.

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25

Liu, Ge, Lichun Kong, Ji Shen, and Gangguo Zhu. "A regio- and stereoselective entry to (Z)-β-halo alkenyl sulfides and their applications to access stereodefined trisubstituted alkenes." Org. Biomol. Chem. 12, no. 14 (2014): 2310–21. http://dx.doi.org/10.1039/c4ob00103f.

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A regio- and stereoselective synthesis of (Z)-β-halo alkenyl sulfides via K2CO3-promoted hydrothiolation of haloalkynes has been reported, permitting a new entry to trisubstituted alkenes featuring the iterative cross-coupling of carbon–halide and carbon–sulfur bonds.
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26

Pérez, Manuel, Tayseer Mahdi, Lindsay J. Hounjet, and Douglas W. Stephan. "Electrophilic phosphonium cations catalyze hydroarylation and hydrothiolation of olefins." Chemical Communications 51, no. 56 (2015): 11301–4. http://dx.doi.org/10.1039/c5cc03572d.

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Electrophilic phosphonium cations (EPCs) are efficient main group catalysts for the hydroarylation and hydrothiolations of olefins under mild conditions, providing a facile route to substituted aniline, bis-arylamine, phenol, furan, thiophene, pyrrole, indole and thioether derivatives.
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27

Barman, Eliezer, Jason Hourezadeh, and Daniel Lim. "Aqueous metal-free hydrothiolation of enamides and enecarbamates." Tetrahedron Letters 60, no. 34 (August 2019): 150951. http://dx.doi.org/10.1016/j.tetlet.2019.150951.

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28

Bo, Zhao, Zeng Ji-Jun, Han Sheng, Tu Dong-Huai, Li Jiang-Wei, Zhang Wei, and Lu Jian. "Base-catalyzed stereoselective hydrophenoxylation and hydrothiolation of hexafluorobutyne." Tetrahedron Letters 61, no. 13 (March 2020): 151693. http://dx.doi.org/10.1016/j.tetlet.2020.151693.

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29

Ananikov, Valentine P, Denis A Malyshev, Irina P Beletskaya, Grigory G Aleksandrov, and Igor L Eremenko. "Nickel(II) Chloride-Catalyzed Regioselective Hydrothiolation of Alkynes." Advanced Synthesis & Catalysis 347, no. 15 (December 2005): 1993–2001. http://dx.doi.org/10.1002/adsc.200505168.

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30

Cabrero-Antonino, Jose R., Antonio Leyva-Perez, and Avelino Corma. "ChemInform Abstract: Iron-Catalyzed Markovnikov Hydrothiolation of Styrenes." ChemInform 43, no. 30 (July 3, 2012): no. http://dx.doi.org/10.1002/chin.201230092.

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31

Shoai, Shiva, Paul Bichler, Baldip Kang, Heather Buckley, and Jennifer A. Love. "Catalytic Alkyne Hydrothiolation with Alkanethiols using Wilkinson's Catalyst." Organometallics 26, no. 24 (November 2007): 5778–81. http://dx.doi.org/10.1021/om700811e.

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32

Sarma, Rupam, Nimmakuri Rajesh, and Dipak Prajapati. "Indium(iii) catalysed substrate selective hydrothiolation of terminal alkynes." Chemical Communications 48, no. 33 (2012): 4014. http://dx.doi.org/10.1039/c2cc30350g.

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33

Tamai, Taichi, Keiko Fujiwara, Shinya Higashimae, Akihiro Nomoto, and Akiya Ogawa. "Gold-Catalyzed Anti-Markovnikov Selective Hydrothiolation of Unactivated Alkenes." Organic Letters 18, no. 9 (April 8, 2016): 2114–17. http://dx.doi.org/10.1021/acs.orglett.6b00746.

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34

Barman, Eliezer, Jason Hourezadeh, and Daniel Lim. "Visible light photoredox-catalyzed hydrothiolation of enamides and enecarbamates." Tetrahedron Letters 61, no. 32 (August 2020): 152201. http://dx.doi.org/10.1016/j.tetlet.2020.152201.

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35

Cao, Changsheng, Lauren R. Fraser, and Jennifer A. Love. "Rhodium-Catalyzed Alkyne Hydrothiolation with Aromatic and Aliphatic Thiols." Journal of the American Chemical Society 127, no. 50 (December 2005): 17614–15. http://dx.doi.org/10.1021/ja055096h.

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36

Kennemur, Jennifer L., Gregory D. Kortman, and Kami L. Hull. "Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines." Journal of the American Chemical Society 138, no. 36 (September 2, 2016): 11914–19. http://dx.doi.org/10.1021/jacs.6b07142.

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37

Menggenbateer, Menggenbateer, Meda Narsireddy, Giovanni Ferrara, Naoko Nishina, Tienan Jin, and Yoshinori Yamamoto. "ChemInform Abstract: Gold-Catalyzed Regiospecific Intermolecular Hydrothiolation of Allenes." ChemInform 41, no. 49 (November 11, 2010): no. http://dx.doi.org/10.1002/chin.201049067.

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38

Kuciński, Krzysztof, Piotr Pawluć, and Grzegorz Hreczycho. "Scandium(III) Triflate-Catalyzedanti-Markovnikov Hydrothiolation of Functionalized Olefins." Advanced Synthesis & Catalysis 357, no. 18 (December 9, 2015): 3936–42. http://dx.doi.org/10.1002/adsc.201500720.

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39

Yadav, J. S., B. V. Subba Reddy, A. Raju, K. Ravindar, and Gakul Baishya. "Hydrothiolation of Unactivated Alkynes Catalyzed by Indium(III) Bromide." Chemistry Letters 36, no. 12 (December 5, 2007): 1474–75. http://dx.doi.org/10.1246/cl.2007.1474.

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40

Hut’ka, Martin, Tetsu Tsubogo, and Shu̅ Kobayashi. "Calcium-Catalyzed Bis-hydrothiolation of Unactivated Alkynes Providing Dithioacetals." Organometallics 33, no. 20 (June 27, 2014): 5626–29. http://dx.doi.org/10.1021/om500442u.

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41

Fraser, Lauren R., Jeffrey Bird, Qiming Wu, Changsheng Cao, Brian O. Patrick, and Jennifer A. Love. "Synthesis, Structure, and Hydrothiolation Activity of Rhodium Pyrazolylborate Complexes." Organometallics 26, no. 23 (November 2007): 5602–11. http://dx.doi.org/10.1021/om700564t.

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42

Ma, Shih-Ting, Chia-Wei Lee, and Wei-Min Liu. "Synthesis of 4-thiol-furanosidic uronate via hydrothiolation reaction." RSC Advances 11, no. 30 (2021): 18409–16. http://dx.doi.org/10.1039/d1ra02110a.

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Uronic acids are not only important building blocks of bioactive molecules but also are widely used in the food and pharmaceutical industries. Its derivative, 4-thiol-furanosidic uronate was successfully synthesized and firstly reported here.
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43

Basu, Basudeb, Kinkar Biswas, Samir Kundu, and Debasish Sengupta. "In Quest of “Stereoselective Switch” for On-Water Hydrothiolation of Terminal Alkynes Using Different Additives and Green Synthesis of Vicinal Dithioethers." Organic Chemistry International 2014 (February 13, 2014): 1–6. http://dx.doi.org/10.1155/2014/358932.

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On-water hydrothiolation reaction between terminal alkyne and thiol has been probed in the presence of various additives. Aromatic alkynes yield corresponding 1-alkenyl sulfides, whereas aliphatic alkynes undergo double-addition yielding vicinal disulfides in good to excellent yields. Formation of 1-alkenyl sulfides proceeds with a high degree of regioselectivity (via anti-Markovnikov addition), and switching the stereoselectivity between E/Z isomers has been noticeably realized in the presence of different additives/promoters.
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44

Schmidt, Elena, Ivan Bidusenko, Igor Ushakov, Nadezhda Protsuk, and Boris Trofimov. "An Easy Access to Sulfur Derivatives of 6,8-Dioxabicyclo[3.2.1]octanes, Naturally Abundant Scaffolds." Synthesis 50, no. 13 (May 3, 2018): 2624–30. http://dx.doi.org/10.1055/s-0036-1591990.

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Sulfur derivatives of 6,8-dioxabicyclo[3.2.1]octanes related to a number of natural products have been synthesized by the click hydrothiolation (AIBN or UV irradiation) of 7-methylene-6,8-dioxabicy­clo[3.2.1]octanes, assembled from acetylene and ketones in a one-pot transition-metal-free synthetic operation. An unusual feature of this free-radical reaction is that it is accelerated in the presence of bases due to involvement of the latter in a competition between the thiol addition and proton-catalyzed isomerization of the starting bicyclooctanes.
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45

Milenin, Sergey A., Fedor V. Drozdov, Elizaveta V. Selezneva, Sofia N. Ardabevskaia, Mikhail I. Buzin, and Aziz M. Muzafarov. "Undecenoic acid-based polydimethylsiloxanes obtained by hydrosilylation and hydrothiolation reactions." Journal of Organometallic Chemistry 907 (February 2020): 121074. http://dx.doi.org/10.1016/j.jorganchem.2019.121074.

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46

Li, Yuanyuan, Jingyu Cai, Mingming Hao, and Zhaohui Li. "Visible light initiated hydrothiolation of alkenes and alkynes over ZnIn2S4." Green Chemistry 21, no. 9 (2019): 2345–51. http://dx.doi.org/10.1039/c9gc00328b.

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47

Feng, Jie, Meifang Lv, Guoping Lu, and Chun Cai. "Efficient Synthesis of Isothiochromene Derivatives by Pd-Catalyzed Hydrothiolation Reaction." European Journal of Organic Chemistry 2014, no. 24 (July 15, 2014): 5312–17. http://dx.doi.org/10.1002/ejoc.201402611.

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48

Rocha, Manuela S. T., Jamal Rafique, Sumbal Saba, Juliano B. Azeredo, Davi Back, Marcelo Godoi, and Antonio L. Braga. "Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe3O4) nanoparticles." Synthetic Communications 47, no. 4 (January 19, 2017): 291–98. http://dx.doi.org/10.1080/00397911.2016.1262421.

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49

Weïwer, Michel, Lydie Coulombel, and Elisabet Duñach. "Regioselective indium(iii) trifluoromethanesulfonate-catalyzed hydrothiolation of non-activated olefins." Chem. Commun., no. 3 (2006): 332–34. http://dx.doi.org/10.1039/b513946e.

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50

Yang, Xiao-Hui, Ryan T. Davison, and Vy M. Dong. "Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes." Journal of the American Chemical Society 140, no. 33 (August 9, 2018): 10443–46. http://dx.doi.org/10.1021/jacs.8b06957.

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