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Journal articles on the topic 'Stereoselective Cyanation of Alkynes'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Peng, Lifen, Zhifang Hu, Hong Wang, et al. "Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes." RSC Advances 10, no. 17 (2020): 10232–44. http://dx.doi.org/10.1039/d0ra01286f.

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Cyanation of alkynes was highlighted. Direct cyanation and hydrocyanation gave alkynyl cyanides and alkenyl nitriles. Dicyanation produced 1,2-dicyano adducts. Cyanofunctionalization afforded functional cyano compounds.

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2

Roy, Tamal, Myungjo J. Kim, Yang Yang, et al. "Carbon Dioxide-Catalyzed Stereoselective Cyanation Reaction." ACS Catalysis 9, no. 7 (2019): 6006–11. http://dx.doi.org/10.1021/acscatal.9b01087.

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3

Rong, Guangwei, Jincheng Mao, Yang Zheng, Ruwei Yao, and Xinfang Xu. "Cu-Catalyzed direct cyanation of terminal alkynes with AMBN or AIBN as the cyanation reagent." Chemical Communications 51, no. 72 (2015): 13822–25. http://dx.doi.org/10.1039/c5cc04987c.

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4

BUTTKE, K., and H. J. NICLAS. "ChemInform Abstract: Studies on Stereoselective Electrophilic Cyanation." ChemInform 30, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.199904096.

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5

Chandra, Prakash, Neha Choudhary, Goutam K. Lahiri, Debabrata Maiti, and Shaikh M. Mobin. "Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions." Asian Journal of Organic Chemistry 10, no. 8 (2021): 1897–937. http://dx.doi.org/10.1002/ajoc.202100182.

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6

Zhu, Peng-Fei, Yi-Xin Si, and Song-Lin Zhang. "An aerobic and green C–H cyanation of terminal alkynes." Organic & Biomolecular Chemistry 18, no. 45 (2020): 9216–20. http://dx.doi.org/10.1039/d0ob01928c.

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7

Ma, Yu-Chuan, Yang Zhang, Cheng-Zhi Gu, Guang-Fen Du та Lin He. "Stereoselective synthesis of α-fluoroacrylonitriles via organocatalytic cyanation of gem-difluoroalkenes and TMSCN". New Journal of Chemistry 43, № 27 (2019): 10985–88. http://dx.doi.org/10.1039/c9nj02370d.

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8

Du, Yan, and Zheng Li. "Copper-catalyzed direct cyanation of terminal alkynes with benzoyl cyanide." Tetrahedron Letters 59, no. 52 (2018): 4622–25. http://dx.doi.org/10.1016/j.tetlet.2018.11.049.

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9

Priebbenow, Daniel L., Robert W. Gable, and Jonathan Baell. "Regio- and Stereoselective Iodoacyloxylations of Alkynes." Journal of Organic Chemistry 80, no. 9 (2015): 4412–18. http://dx.doi.org/10.1021/acs.joc.5b00250.

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10

Li, Zhaodong, Andrés García-Domínguez, and Cristina Nevado. "Pd-Catalyzed Stereoselective Carboperfluoroalkylation of Alkynes." Journal of the American Chemical Society 137, no. 36 (2015): 11610–13. http://dx.doi.org/10.1021/jacs.5b07432.

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11

Lei, Jian, Huaxin Gao, Miaoling Huang, Xiao Liu, Yangfan Mao, and Xiaolan Xie. "Copper-catalyzed stereoselective alkylhydrazination of alkynes." Chemical Communications 56, no. 6 (2020): 920–23. http://dx.doi.org/10.1039/c9cc07998j.

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12

Ning, Yongquan, Qinghe Ji, Peiqiu Liao, Edward A. Anderson, and Xihe Bi. "Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes." Angewandte Chemie International Edition 56, no. 44 (2017): 13805–8. http://dx.doi.org/10.1002/anie.201705122.

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13

Barrado, Alejandro G., Adam Zieliński, Richard Goddard, and Manuel Alcarazo. "Regio- and Stereoselective Chlorocyanation of Alkynes." Angewandte Chemie International Edition 56, no. 43 (2017): 13401–5. http://dx.doi.org/10.1002/anie.201705851.

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14

Li, Zhaodong, Andrés García-Domínguez, and Cristina Nevado. "Nickel-Catalyzed Stereoselective Dicarbofunctionalization of Alkynes." Angewandte Chemie International Edition 55, no. 24 (2016): 6938–41. http://dx.doi.org/10.1002/anie.201601296.

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15

Li, Zhaodong, Andrés García-Domínguez, and Cristina Nevado. "Nickel-Catalyzed Stereoselective Dicarbofunctionalization of Alkynes." Angewandte Chemie 128, no. 24 (2016): 7052–55. http://dx.doi.org/10.1002/ange.201601296.

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16

Nishimoto, Yoshihiro, Midori Takeuchi, Makoto Yasuda, and Akio Baba. "Regio- and Stereoselective Carbobismuthination of Alkynes." Angewandte Chemie 124, no. 4 (2011): 1075–78. http://dx.doi.org/10.1002/ange.201107127.

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17

Ning, Yongquan, Qinghe Ji, Peiqiu Liao, Edward A. Anderson, and Xihe Bi. "Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes." Angewandte Chemie 129, no. 44 (2017): 13993–96. http://dx.doi.org/10.1002/ange.201705122.

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18

Barrado, Alejandro G., Adam Zieliński, Richard Goddard, and Manuel Alcarazo. "Regio- and Stereoselective Chlorocyanation of Alkynes." Angewandte Chemie 129, no. 43 (2017): 13586–90. http://dx.doi.org/10.1002/ange.201705851.

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19

Nishimoto, Yoshihiro, Midori Takeuchi, Makoto Yasuda, and Akio Baba. "Regio- and Stereoselective Carbobismuthination of Alkynes." Angewandte Chemie International Edition 51, no. 4 (2011): 1051–54. http://dx.doi.org/10.1002/anie.201107127.

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20

Liu, Wenfeng, and Wangqing Kong. "Ni-Catalyzed stereoselective difunctionalization of alkynes." Organic Chemistry Frontiers 7, no. 23 (2020): 3941–55. http://dx.doi.org/10.1039/d0qo01097a.

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We summarize the progress of the nickel-catalyzed alkyne difunctionalization reaction for the synthesis of tri- and tetrasubstituted olefins, with an emphasis on the strategy and control of stereochemistry.

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21

Jiang, H., Z. Chen, J. Li, S. Zhu, Y. Li, and C. Qi. "Regio- and Stereoselective Difunctionalization of Alkynes." Synfacts 2010, no. 11 (2010): 1278. http://dx.doi.org/10.1055/s-0030-1258800.

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22

Wu, Guojiao, and Axel Jacobi von Wangelin. "Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes." Chemical Science 9, no. 7 (2018): 1795–802. http://dx.doi.org/10.1039/c7sc04916a.

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Stereoselective additions of functionalized reagents to unsaturated hydrocarbons are attractive due to the high atom economy, modularity and rapid generation of complexity. We report a stereoselective cobalt-catalyzed (E)-halofluoroalkylation of alkynes/alkenes that under mild conditions (2 mol% cat., 20 °C, acetone/water, 3 h). This reaction operates via a radical chain mechanism involving terminal halogen atom transfer which obviates the need for a stoichiometric sacrificial reductant.

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23

Lukashev, Nikolai V., Alexei V. Kazantsev, Anatolii A. Borisenko та Irina P. Beletskaya. "Cyanation of nucleophilic alkynes: easy approach to element-substituted α-cyanoenamines". Tetrahedron 57, № 52 (2001): 10309–17. http://dx.doi.org/10.1016/s0040-4020(01)01056-0.

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24

Okamoto, Kazuhiro, Masahito Watanabe, Naoki Sakata, Masahito Murai, and Kouichi Ohe. "Copper-Catalyzed C–H Cyanation of Terminal Alkynes with Cyanogen Iodide." Organic Letters 15, no. 22 (2013): 5810–13. http://dx.doi.org/10.1021/ol402863g.

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25

Oestreich, Martin, Roland Fröhlich, and Dieter Hoppe. "(−)-Sparteine-mediated stereoselective intramolecular carbolithiation of alkynes." Tetrahedron Letters 39, no. 13 (1998): 1745–48. http://dx.doi.org/10.1016/s0040-4039(98)00085-9.

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26

Komeyama, Kimihiro, Ryota Asakura, Hiroshi Fukuoka, and Ken Takaki. "Cobalt-catalyzed intermolecular stereoselective bisbenzylation of alkynes." Tetrahedron Letters 56, no. 13 (2015): 1735–37. http://dx.doi.org/10.1016/j.tetlet.2015.02.101.

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27

Michaelides, Iacovos N., and Darren J. Dixon. "Catalytic Stereoselective Semihydrogenation of Alkynes toE-Alkenes." Angewandte Chemie International Edition 52, no. 3 (2012): 806–8. http://dx.doi.org/10.1002/anie.201208120.

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28

Gregori, Bernhard J., Michal Nowakowski, Anke Schoch, et al. "Stereoselective Chromium‐Catalyzed Semi‐Hydrogenation of Alkynes." ChemCatChem 12, no. 21 (2020): 5359–63. http://dx.doi.org/10.1002/cctc.202000994.

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29

Li, Zhaodong, Estíbaliz Merino, and Cristina Nevado. "Stereoselective Carboperfluoroalkylation of Internal Alkynes: Mechanistic Insights." Topics in Catalysis 60, no. 8 (2017): 545–53. http://dx.doi.org/10.1007/s11244-017-0743-y.

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30

Wang, Hannan, Pengbing Mi, Wanjun Zhao, Ravi Kumar, and Xihe Bi. "Silver-Mediated Direct C–H Cyanation of Terminal Alkynes with N-Isocyanoiminotriphenylphosphorane." Organic Letters 19, no. 20 (2017): 5613–16. http://dx.doi.org/10.1021/acs.orglett.7b02743.

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31

Liu, Ting, Jie-Ping Wan та Yunyun Liu. "Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of (E)- and (Z)-β-cyano enones". Chemical Communications 57, № 72 (2021): 9112–15. http://dx.doi.org/10.1039/d1cc03292e.

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The C–N bond cyanation of tertiary enaminones has been realized for the stereoselective synthesis of both (E)- and (Z)-β-cyano enones under mild metal-free conditions, providing highly practical approaches for the synthesis of β-cyano enones.

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32

Fernández, Rosario, Eloísa Martín-Zamora, Carmen Pareja та José M. Lassaletta. "Stereoselective Nucleophilic Formylation and Cyanation of α-Alkoxy- and α-Aminoaldehydes". Journal of Organic Chemistry 66, № 15 (2001): 5201–7. http://dx.doi.org/10.1021/jo015711+.

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33

Dodero, Verónica I., Liliana C. Koll, Sandra D. Mandolesi, and Julio C. Podestá. "Stereoselective hydrostannation of substituted alkynes with trineophyltin hydride." Journal of Organometallic Chemistry 650, no. 1-2 (2002): 173–80. http://dx.doi.org/10.1016/s0022-328x(02)01213-5.

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34

Pedersen, Palle J., Jonas Henriksen, Charlotte H. Gotfredsen, and Mads H. Clausen. "Regio- and stereoselective hydrosilylation of immobilized terminal alkynes." Tetrahedron Letters 49, no. 43 (2008): 6220–23. http://dx.doi.org/10.1016/j.tetlet.2008.08.043.

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35

Goossen, Lukas J., Mathieu Blanchot, Claus Brinkmann, Käthe Goossen, Ralph Karch, and Andreas Rivas-Nass. "Ru-Catalyzed Stereoselective Addition of Imides to Alkynes." Journal of Organic Chemistry 71, no. 25 (2006): 9506–9. http://dx.doi.org/10.1021/jo061966h.

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36

Yus, M., F. Alonso, and I. Osante. "Stereoselective Semihydrogenation of Alkynes by Nickel(0) Nanoparticles." Synfacts 2006, no. 5 (2006): 0476. http://dx.doi.org/10.1055/s-2006-934432.

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37

Veenboer, Richard M. P., Stéphanie Dupuy, and Steven P. Nolan. "Stereoselective Gold(I)-Catalyzed Intermolecular Hydroalkoxlation of Alkynes." ACS Catalysis 5, no. 2 (2015): 1330–34. http://dx.doi.org/10.1021/cs501976s.

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38

Hojo, Makoto, Yoshio Murakami, Hidenori Aihara, Rie Sakuragi, Yu Baba, and Akira Hosomi. "Iron-Catalyzed Regio- and Stereoselective Carbolithiation of Alkynes." Angewandte Chemie International Edition 40, no. 3 (2001): 621–23. http://dx.doi.org/10.1002/1521-3773(20010202)40:3<621::aid-anie621>3.0.co;2-o.

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39

Liu, Jie‐Jie, Ling Lan, Yu‐Ting Gao, et al. "Visible‐Light‐Mediated Stereoselective 1,2‐Iodoalkylation of Alkynes." Advanced Synthesis & Catalysis 361, no. 6 (2019): 1283–88. http://dx.doi.org/10.1002/adsc.201801636.

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40

Nishimoto, Yoshihiro, Midori Takeuchi, Makoto Yasuda, and Akio Baba. "ChemInform Abstract: Regio- and Stereoselective Carbobismuthination of Alkynes." ChemInform 43, no. 23 (2012): no. http://dx.doi.org/10.1002/chin.201223085.

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41

Priebbenow, Daniel L., Robert W. Gable, and Jonathan Baell. "ChemInform Abstract: Regio- and Stereoselective Iodoacyloxylations of Alkynes." ChemInform 46, no. 37 (2015): no. http://dx.doi.org/10.1002/chin.201537082.

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42

Li, Zhaodong, Andres Garcia-Dominguez, and Cristina Nevado. "ChemInform Abstract: Pd-Catalyzed Stereoselective Carboperfluoroalkylation of Alkynes." ChemInform 47, no. 9 (2016): no. http://dx.doi.org/10.1002/chin.201609050.

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43

Gu, Yiting, Yaya Duan, Yangyang Shen, and Ruben Martin. "Stereoselective Base‐Catalyzed 1,1‐Silaboration of Terminal Alkynes." Angewandte Chemie International Edition 59, no. 5 (2020): 2061–65. http://dx.doi.org/10.1002/anie.201913544.

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44

Hojo, Makoto, Yoshio Murakami, Hidenori Aihara, Rie Sakuragi, Yu Baba, and Akira Hosomi. "Iron-Catalyzed Regio- and Stereoselective Carbolithiation of Alkynes." Angewandte Chemie 113, no. 3 (2001): 641–43. http://dx.doi.org/10.1002/1521-3757(20010202)113:3<641::aid-ange641>3.0.co;2-v.

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45

Weber, Andressa C. H., Felipe L. Coelho, Ricardo F. Affeldt, and Paulo H. Schneider. "Visible-Light Promoted Stereoselective Arylselanyl Functionalization of Alkynes." European Journal of Organic Chemistry 2018, no. 47 (2018): 6738–42. http://dx.doi.org/10.1002/ejoc.201801303.

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46

Hirai, Takayoshi, Hitoshi Kuniyasu, and Nobuaki Kambe. "Pt-Catalyzed Regio- and Stereoselective Thienylthiolation of Alkynes." Chemistry Letters 33, no. 9 (2004): 1148–49. http://dx.doi.org/10.1246/cl.2004.1148.

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47

Kuniyasu, Hitoshi, Nobuaki Kambe, Takayoshi Hirai, Shigehito Asano, and Jun Terao. "Pt-Catalyzed Regio- and Stereoselective Furylthiolation of Alkynes." Synlett, no. 7 (2005): 1161–63. http://dx.doi.org/10.1055/s-2005-865232.

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48

Xiao, Fuhong, Dahan Wang, Shanshan Yuan, Huawen Huang, and Guo-Jun Deng. "Iodine-promoted stereoselective amidosulfenylation of electron-deficient alkynes." RSC Advances 8, no. 41 (2018): 23319–22. http://dx.doi.org/10.1039/c8ra04374d.

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49

Gu, Yiting, Yaya Duan, Yangyang Shen, and Ruben Martin. "Stereoselective Base‐Catalyzed 1,1‐Silaboration of Terminal Alkynes." Angewandte Chemie 132, no. 5 (2019): 2077–81. http://dx.doi.org/10.1002/ange.201913544.

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50

Liu, Jin-Biao, Miaofeng Ren, Xiaojing Lai, and Guanyinsheng Qiu. "Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes." Chemical Communications 57, no. 35 (2021): 4259–62. http://dx.doi.org/10.1039/d1cc00870f.

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In this work, by using N-methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed acyl nitrene/alkyne metalation-based chloramidation is reported for the synthesis of isoindol-5-ones.

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