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Journal articles on the topic 'Hydroalkoxylation'

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Author: Grafiati
Published: 4 June 2021
Last updated: 19 February 2022

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1

Li, Zhi, and Wen-Bin Xie. "Asymmetric Synthesis of Ethers by Catalytic Alkene Hydro­alkoxy­lation." Synthesis 52, no. 15 (April 14, 2020): 2127–46. http://dx.doi.org/10.1055/s-0039-1690874.

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Many chiral ethers have important physiological activities. Although many asymmetric hydroalkoxylations of olefins with alcohols or phenols have been developed to make chiral ethers, challenges still remain in achieving high reactivity and selectivity over an ever-increasing diversity of alkenes and alcohols. In this review, recent developments on catalytic asymmetric alkene hydroalkoxylations are summarized based on the substitution patterns of alkenes.1 Introduction2 Asymmetric Hydroalkoxylation of Non-Activated Alkenes2.1 Intramolecular Additions2.2 Intermolecular Additions3 Asymmetric Hydroalkoxylation of Enol Ethers3.1 Intramolecular Additions3.2 Intermolecular Additions4 Asymmetric Hydroalkoxylation of α,β-Unsaturated Carbonyl Compounds4.1 α,β-Unsaturated Ketones and Aldehydes as Substrates4.2 α,β-Unsaturated Esters, Amides and Carboxylic Acids as Substrates5 Asymmetric Hydroalkoxylation of Allenes5.1 Intramolecular Additions5.2 Intermolecular Additions6 Conclusion
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2

Kena Diba, Anastasie, Jeanne-Marie Begouin, and Meike Niggemann. "Calcium catalyzed hydroalkoxylation." Tetrahedron Letters 53, no. 49 (December 2012): 6629–32. http://dx.doi.org/10.1016/j.tetlet.2012.08.129.

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3

Nishina, Naoko, and Yoshinori Yamamoto. "Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination." Tetrahedron Letters 49, no. 33 (August 2008): 4908–11. http://dx.doi.org/10.1016/j.tetlet.2008.05.152.

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4

Notar Francesco, Irene, Bastien Cacciuttolo, Mathieu Pucheault, and Sylvain Antoniotti. "Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents." Green Chemistry 17, no. 2 (2015): 837–41. http://dx.doi.org/10.1039/c4gc01990c.

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5

Gao, Shu-Shan, Marc Garcia-Borràs, Joyann S. Barber, Yang Hai, Abing Duan, Neil K. Garg, K. N. Houk, and Yi Tang. "Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation." Journal of the American Chemical Society 139, no. 10 (March 2017): 3639–42. http://dx.doi.org/10.1021/jacs.7b01089.

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6

Camacho, Drexel H., Itaru Nakamura, Shinichi Saito, and Yoshinori Yamamoto. "Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes." Angewandte Chemie International Edition 38, no. 22 (November 15, 1999): 3365–67. http://dx.doi.org/10.1002/(sici)1521-3773(19991115)38:22<3365::aid-anie3365>3.0.co;2-5.

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7

Cui, Dong-Mei, Zhi-Ling Zheng, and Chen Zhang. "Gold-Catalyzed Hydroalkoxylation of Alkoxyallenes." Journal of Organic Chemistry 74, no. 3 (February 6, 2009): 1426–27. http://dx.doi.org/10.1021/jo802513a.

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8

Diba, Anastasie Kena, Jeanne-Marie Begouin, and Meike Niggemann. "ChemInform Abstract: Calcium-Catalyzed Hydroalkoxylation." ChemInform 44, no. 13 (March 18, 2013): no. http://dx.doi.org/10.1002/chin.201313083.

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9

Notar Francesco, Irene, Bastien Cacciuttolo, Oana Pascu, Cyril Aymonier, Mathieu Pucheault, and Sylvain Antoniotti. "Simple salts of abundant metals (Fe, Bi, and Ti) supported on montmorillonite as efficient and recyclable catalysts for regioselective intramolecular and intermolecular hydroalkoxylation reactions of double bonds and tandem processes." RSC Advances 6, no. 24 (2016): 19807–18. http://dx.doi.org/10.1039/c5ra25176a.

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10

Gao, Erhui, Cheng Peng, Jingyi Zhang, Xiao-Na Wang, and Junbiao Chang. "Metal-free hydroalkoxylation of ynesulfonamides with esters." Organic & Biomolecular Chemistry 19, no. 10 (2021): 2182–85. http://dx.doi.org/10.1039/d0ob02575e.

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11

Hack, Daniel, Pankaj Chauhan, Kristina Deckers, Yusuke Mizutani, Gerhard Raabe, and Dieter Enders. "Combining silver- and organocatalysis: an enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles." Chemical Communications 51, no. 12 (2015): 2266–69. http://dx.doi.org/10.1039/c4cc09495f.

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12

Catti, L., and K. Tiefenbacher. "Intramolecular hydroalkoxylation catalyzed inside a self-assembled cavity of an enzyme-like host structure." Chemical Communications 51, no. 5 (2015): 892–94. http://dx.doi.org/10.1039/c4cc08211g.

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13

Vuong, Khuong Q., Chin M. Wong, Mohan Bhadbhade, and Barbara A. Messerle. "Bi- and tri-metallic Rh and Ir complexes containing click derived bis- and tris-(pyrazolyl-1,2,3-triazolyl) N–N′ donor ligands and their application as catalysts for the dihydroalkoxylation of alkynes." Dalton Trans. 43, no. 20 (2014): 7540–53. http://dx.doi.org/10.1039/c3dt53295j.

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14

Liu, Congrong, Jin Xu, Lianghui Ding, Haiyun Zhang, Yunbo Xue, and Fulai Yang. "Au-Catalyzed tandem intermolecular hydroalkoxylation/Claisen rearrangement between allylic alcohols and chloroalkynes." Organic & Biomolecular Chemistry 17, no. 18 (2019): 4435–39. http://dx.doi.org/10.1039/c9ob00151d.

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15

Goodwin, Justin A., and Aaron Aponick. "Correction: Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes." Chemical Communications 52, no. 40 (2016): 6731. http://dx.doi.org/10.1039/c6cc90121b.

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16

Sun, Zhen, Zheng Li, and Wei-Wei Liao. "An organocatalytic hydroalkoxylation/Claisen rearrangement/Michael addition tandem sequence: divergent synthesis of multi-substituted 2,3-dihydrofurans and 2,3-dihydropyrroles from cyanohydrins." Green Chemistry 21, no. 7 (2019): 1614–18. http://dx.doi.org/10.1039/c8gc03978j.

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17

Zhang, Jian Ting, Cheng Lin Zhu, Jun Min Feng, Rui Wang, Shuang Ping Huang, and Xiao Ji Wang. "Effective Hydroalkoxylation/Cyclization of Alkynyl Alcohol Catalyzed by In(OTf)3." Advanced Materials Research 1033-1034 (October 2014): 541–43. http://dx.doi.org/10.4028/www.scientific.net/amr.1033-1034.541.

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18

Cloutier, Mélissa, Marius Mamone, and Jean-François Paquin. "Drastic fluorine effect: complete reversal of the selectivity in the Au-catalyzed hydroalkoxylation reaction of fluorinated haloalkynes." Chemical Communications 56, no. 44 (2020): 5969–72. http://dx.doi.org/10.1039/d0cc02009e.

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19

Kaya, Uğur, Pankaj Chauhan, Daniel Hack, Kristina Deckers, Rakesh Puttreddy, Kari Rissanen, and Dieter Enders. "Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis." Chemical Communications 52, no. 8 (2016): 1669–72. http://dx.doi.org/10.1039/c5cc09592a.

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An enantioselective Michael addition/hydroalkoxylation reaction between 2-hydroxy-1,4-naphthoquinones and alkyne-tethered nitroalkenes catalysed by a cinchona-derived squaramide/silver(i) salt has been developed.
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20

Goodwin, Justin A., and Aaron Aponick. "Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes." Chemical Communications 51, no. 42 (2015): 8730–41. http://dx.doi.org/10.1039/c5cc00120j.

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21

Zamanian, Sara, and Ali Nemati Kharat. "Catalytic Olefin Hydroalkoxylation by Nano Particles of Pollucite." Australian Journal of Chemistry 68, no. 6 (2015): 981. http://dx.doi.org/10.1071/ch14492.

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The catalytic hydroalkoxylation of α,β-unsaturated esters, nitriles, and ethers with aliphatic and aromatic alcohols over pollucite using thermal and microwave-assisted methods was investigated. To study the effect of the alcohol structures on the mechanism of the hydroalkoxylation reaction, different alcohols, such as methanol to butanol, cyclohexanol, phenol, and 2-ethylhexanol were used. The activities of pollucite, in contrast to other basic solids, were scarcely affected by the presence of air and moisture. The correlation between alcohol acidity and reaction activity is discussed. The prepared pollucite was characterized by X‐ray diffraction, volumetric nitrogen adsorption surface area analysis, and CO2 temperature‐programmed desorption. Scanning electron microscopy analysis revealed that the size of the modified nano catalyst particles was under 40 nm.
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22

Dince, Clément C., Roy A. Meoded, and Donald Hilvert. "Synthesis and characterization of catalytically active thiazolium gold(i)-carbenes." Chemical Communications 53, no. 54 (2017): 7585–87. http://dx.doi.org/10.1039/c7cc03791k.

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23

Discolo, Christopher A., Eric E. Touney, and Sergey V. Pronin. "Catalytic Asymmetric Radical–Polar Crossover Hydroalkoxylation." Journal of the American Chemical Society 141, no. 44 (October 23, 2019): 17527–32. http://dx.doi.org/10.1021/jacs.9b10645.

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24

Ketcham, John M., Berenger Biannic, and Aaron Aponick. "The tandem intermolecular hydroalkoxylation/claisen rearrangement." Chem. Commun. 49, no. 39 (2013): 4157–59. http://dx.doi.org/10.1039/c2cc37166a.

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25

Gharpure, Santosh J., Santosh K. Nanda, and Dipak J. Fartade. "Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition." Organic & Biomolecular Chemistry 17, no. 39 (2019): 8806–10. http://dx.doi.org/10.1039/c9ob02030f.

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The first examples of highly diastereoselective tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition are described for the synthesis of medium ring heterocycle-fused chromenes.
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26

Nakate, Ashwini K., Madhukar S. Pratapure, and Ravindar Kontham. "Bismuth(iii)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans." Organic & Biomolecular Chemistry 16, no. 17 (2018): 3229–40. http://dx.doi.org/10.1039/c8ob00368h.

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2-(Hetero)aryl tetrahydrofurans and tetrahydropyrans were successfully synthesized using Bi(OTf)3-catalyzed hydroalkoxylation (cycloisomerization) of alkynols (via 5 or 6 exo-dig cyclization) and intermolecular (hetero)arylation.
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27

Counsell, Andrew J., Mingfeng Yu, Mengying Shi, Angus T. Jones, James M. Batten, Peter Turner, Matthew H. Todd, and Peter J. Rutledge. "Copper(ii) complexes of N-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity." Dalton Transactions 50, no. 11 (2021): 3931–42. http://dx.doi.org/10.1039/d0dt03736b.

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Copper(ii) complexes of cyclam ligands with 1, 2, 3 or 4 pendant alkynes have been prepared and characterised crystallographically and spectroscopically. An unexpected hydroalkoxylation reaction is observed, affording an enol ether from the alkyne.
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28

Chou, Ting-Hung, Bo-Hung Yu, and Rong-Jie Chein. "ZnI2/Zn(OTf)2-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization." Chemical Communications 55, no. 90 (2019): 13522–25. http://dx.doi.org/10.1039/c9cc07242j.

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A mild and efficient combined-acid system using a zinc(ii) salt [ZnI2 or Zn(OTf)2] and TsOH was investigated for intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, and hydroarylation and polyene cyclizations.
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29

Kim, Mijong, Suyeon Lee, Kiseong Kim, Dongwoo Shin, Hyunwoo Kim, and Hyunjoon Song. "A highly Lewis-acidic Pd(iv) surface on Pd@SiO2 nanocatalysts for hydroalkoxylation reactions." Chem. Commun. 50, no. 95 (2014): 14938–41. http://dx.doi.org/10.1039/c4cc05112b.

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The Pd(iv) species, generated on the surface of Pd@SiO2 nanocatalysts via oxidation with iodobenzene dichloride (PhICl2) or N-chlorosuccinimide (NCS), showed high reactivity and superior stability for hydroalkoxylation reactions.
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30

Coutant, Eloi, Paul C. Young, Graeme Barker, and Ai-Lan Lee. "Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols." Beilstein Journal of Organic Chemistry 9 (September 4, 2013): 1797–806. http://dx.doi.org/10.3762/bjoc.9.209.

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A gold(I)-catalysed reaction of allylic alcohols and phenols produces chromans regioselectively via a one-pot Friedel–Crafts allylation/intramolecular hydroalkoxylation sequence. The reaction is mild, practical and tolerant of a wide variety of substituents on the phenol.
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31

Tokunaga, Makoto, Akiyuki Hamasaki, Eiji Yamamoto, and Hisashi Itoh. "Metal Complexes-catalyzed Hydrolysis, Alcoholysis, and Hydroalkoxylation." Journal of Synthetic Organic Chemistry, Japan 68, no. 7 (2010): 738–44. http://dx.doi.org/10.5059/yukigoseikyokaishi.68.738.

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32

Zhou, Bo, Long Li, Xin Liu, Tong-De Tan, Jinxian Liu, and Long-Wu Ye. "Yttrium-Catalyzed Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement." Journal of Organic Chemistry 82, no. 19 (September 11, 2017): 10149–57. http://dx.doi.org/10.1021/acs.joc.7b01612.

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33

Kadota, Isao, Leopold Mpaka Lutete, Akinori Shibuya, and Yoshinori Yamamoto. "Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes." Tetrahedron Letters 42, no. 35 (August 2001): 6207–10. http://dx.doi.org/10.1016/s0040-4039(01)01207-2.

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34

Camacho, Drexel H., Itaru Nakamura, Shinichi Saito, and Yoshinori Yamamoto. "ChemInform Abstract: Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes." ChemInform 31, no. 9 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.200009079.

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35

Widenhoefer, R., and Z. Zhang. "First Catalytic Enantioselective Intramolecular Hydroalkoxylation of Allenes." Synfacts 2007, no. 3 (March 2007): 0304. http://dx.doi.org/10.1055/s-2007-968182.

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36

de la Cruz-Martínez, Felipe, Marc Martínez de Sarasa Buchaca, Juan Fernández-Baeza, Luis F. Sánchez-Barba, Ana M. Rodríguez, José A. Castro-Osma, and Agustín Lara-Sánchez. "Zinc-Catalyzed Hydroalkoxylation/Cyclization of Alkynyl Alcohols." Inorganic Chemistry 60, no. 7 (March 15, 2021): 5322–32. http://dx.doi.org/10.1021/acs.inorgchem.1c00309.

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37

González-Belman, Oscar, Artur Brotons-Rufes, Michele Tomasini, Laura Falivene, Lucia Caporaso, Jose Jiménez-Halla, and Albert Poater. "Towards Dual-Metal Catalyzed Hydroalkoxylation of Alkynes." Catalysts 11, no. 6 (June 2, 2021): 704. http://dx.doi.org/10.3390/catal11060704.

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Poly (vinyl ethers) are compounds with great value in the coating industry due to exhibiting properties such as high viscosity, soft adhesiveness, resistance to saponification and solubility in water and organic solvents. However, the main challenge in this field is the synthesis of vinyl ether monomers that can be synthetized by methodologies such as vinyl transfer, reduction of vinyl phosphate ether, isomerization, hydrogenation of acetylenic ethers, elimination, addition of alcohols to alkyne species etc. Nevertheless, the most successful strategy to access to vinyl ether derivatives is the addition of alcohols to alkynes catalyzed by transition metals such as molybdenum, tungsten, ruthenium, palladium, platinum, gold, silver, iridium and rhodium, where gold-NHC catalysts have shown the best results in vinyl ether synthesis. Recently, the hydrophenoxylation reaction was found to proceed through a digold-assisted process where the species that determine the rate of the reaction are PhO-[Au(IPr)] and alkyne-[Au(IPr)]. Later, the improvement of the hydrophenoxylation reaction by using a mixed combination of Cu-NHC and Au-NHC catalysts was also reported. DFT studies confirmed a cost-effective method for the hydrophenoxylation reaction and located the rate-determining step, which turned out to be quite sensitive to the sterical hindrance due to the NHC ligands.
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38

Shibuya, Masatoshi, Shoji Fujita, and Yoshihiko Yamamoto. "Intramolecular Hydroalkoxylation/Reduction and Hydroamination/Reduction of Unactivated Alkynes Using a Silane–Iodine Catalytic System." Synthesis 49, no. 18 (May 24, 2017): 4199–204. http://dx.doi.org/10.1055/s-0036-1588436.

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A transition-metal-free silane–iodine catalytic system comprising I2 and Et3SiH promotes intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes. This system allows the reaction to proceed at room temperature affording 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofuran with high diastereoselectivity.
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39

Rocard, Lou, Donghuang Chen, Adrien Stadler, Hailong Zhang, Richard Gil, Sophie Bezzenine, and Jerome Hannedouche. "Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes." Catalysts 11, no. 6 (May 25, 2021): 674. http://dx.doi.org/10.3390/catal11060674.

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This review summarizes the most noteworthy achievements in the field of C–O and C–N bond formation by hydroalkoxylation and hydroamination reactions on unactivated alkenes (including 1,2- and 1,3-dienes) promoted by earth-abundant 3d transition metal catalysts based on manganese, iron, cobalt, nickel, copper and zinc. The relevant literature from 2012 until early 2021 has been covered.
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40

Komeyama, Kimihiro, Takayuki Morimoto, Yuushou Nakayama, and Ken Takaki. "Cationic iron-catalyzed intramolecular hydroalkoxylation of unactivated olefins." Tetrahedron Letters 48, no. 18 (April 2007): 3259–61. http://dx.doi.org/10.1016/j.tetlet.2007.03.004.

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41

Jean, Alexandre, Jacques Rouden, Jacques Maddaluno, Michaël De Paolis, and Jérôme Blanchet. "Catalytic and metal-free intramolecular hydroalkoxylation of alkynes." Tetrahedron Letters 60, no. 7 (February 2019): 534–37. http://dx.doi.org/10.1016/j.tetlet.2019.01.020.

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42

Tran, Gaël, and Clément Mazet. "Ni-Catalyzed Regioselective Hydroalkoxylation of Branched 1,3-Dienes." Organic Letters 21, no. 22 (October 25, 2019): 9124–27. http://dx.doi.org/10.1021/acs.orglett.9b03511.

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43

Iio, Kei, Shusuke Sachimori, Tomomi Watanabe, and Haruhiko Fuwa. "Ruthenium-Catalyzed Intramolecular Double Hydroalkoxylation of Internal Alkynes." Organic Letters 20, no. 24 (December 5, 2018): 7851–55. http://dx.doi.org/10.1021/acs.orglett.8b03368.

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44

Ramachary, Dhevalapally B., and Rumpa Mondal. "Direct organocatalytic hydroalkoxylation of α,β-unsaturated ketones." Tetrahedron Letters 47, no. 44 (October 2006): 7689–93. http://dx.doi.org/10.1016/j.tetlet.2006.08.134.

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45

Belting, Volker, and Norbert Krause. "Gold-Catalyzed Tandem Cycloisomerization−Hydroalkoxylation of Homopropargylic Alcohols." Organic Letters 8, no. 20 (September 2006): 4489–92. http://dx.doi.org/10.1021/ol061751u.

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46

Ke, Fang, Zhengkai Li, Haifeng Xiang, and Xiangge Zhou. "Catalytic hydroalkoxylation of alkenes by iron(III) catalyst." Tetrahedron Letters 52, no. 2 (January 2011): 318–20. http://dx.doi.org/10.1016/j.tetlet.2010.11.036.

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47

Murayama, Hiroaki, Kazunori Nagao, Hirohisa Ohmiya, and Masaya Sawamura. "Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes." Organic Letters 17, no. 9 (April 7, 2015): 2039–41. http://dx.doi.org/10.1021/acs.orglett.5b00758.

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48

Talluri, Siva Kumar, and Arumugam Sudalai. "NBS-Catalyzed Hydroamination and Hydroalkoxylation of Activated Styrenes." Organic Letters 7, no. 5 (March 2005): 855–57. http://dx.doi.org/10.1021/ol047402m.

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49

Zhang, Zhibin, and Ross A Widenhoefer. "Gold(I)-Catalyzed Intramolecular Enantioselective Hydroalkoxylation of Allenes." Angewandte Chemie International Edition 46, no. 1-2 (January 2007): 283–85. http://dx.doi.org/10.1002/anie.200603260.

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50

Ketcham, John M., Berenger Biannic, and Aaron Aponick. "ChemInform Abstract: The Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement." ChemInform 44, no. 37 (August 22, 2013): no. http://dx.doi.org/10.1002/chin.201337056.

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