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Journal articles on the topic 'Allylic fluorides'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 May 2025

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1

Ernet, Thomas, and Günter Haufe. "Allylic Hydroxylation of Vinyl Fluorides." Synthesis 1997, no. 08 (1997): 953–56. http://dx.doi.org/10.1055/s-1997-1279.

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2

Vilotijevic, Ivan, Markus Lange, and You Zi. "Latent (Pro)Nucleophiles in Enantioselective Lewis Base Catalyzed Allylic Substitutions." Synlett 31, no. 13 (2020): 1237–43. http://dx.doi.org/10.1055/s-0040-1707130.

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The use of latent nucleophiles, which are molecules that are not nucleophilic but can be activated to act as a nucleophile at an opportune time during the reaction, expands the scope of Lewis base catalyzed reactions. Here, we provide an overview of the concept and show examples of applications to N- and C-centered nucleophiles in allylic substitutions. N- and C-silyl compounds are superior latent (pro)nucleophiles in Lewis base catalyzed reactions with allylic fluorides in which the formation of the strong Si–F bond serves as the driving force for the reactions. The latent (pro)nucleophiles e

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3

Thibaudeau, S�bastien, Robert Fuller, and V�ronique Gouverneur. "Stereoselective synthesis of internal allylic fluorides." Organic & Biomolecular Chemistry 2, no. 8 (2004): 1110. http://dx.doi.org/10.1039/b402097a.

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4

Benedetto, Elena, Massaba Keita, Matthew Tredwell, Charlotte Hollingworth, John M. Brown, and Véronique Gouverneur. "Platinum-Catalyzed Substitution of Allylic Fluorides." Organometallics 31, no. 4 (2012): 1408–16. http://dx.doi.org/10.1021/om201029m.

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5

Hazari, Amaruka, Véronique Gouverneur, and John M Brown. "Palladium-Catalyzed Substitution of Allylic Fluorides." Angewandte Chemie International Edition 48, no. 7 (2009): 1296–99. http://dx.doi.org/10.1002/anie.200804310.

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6

Hazari, Amaruka, Véronique Gouverneur, and John M Brown. "Palladium-Catalyzed Substitution of Allylic Fluorides." Angewandte Chemie 121, no. 7 (2009): 1322–25. http://dx.doi.org/10.1002/ange.200804310.

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7

Hamel, Jean-Denys, та Jean-François Paquin. "Activation of C–F bonds α to C–C multiple bonds". Chemical Communications 54, № 73 (2018): 10224–39. http://dx.doi.org/10.1039/c8cc05108a.

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8

Zi, You, Markus Lange, and Ivan Vilotijevic. "Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a C-silyl latent pronucleophile." Chemical Communications 56, no. 42 (2020): 5689–92. http://dx.doi.org/10.1039/d0cc01815e.

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9

Chen, Xin, Shuai Zhao, Zhi-Li Chen, Xue Rui, and Ming-Mei Gao. "Asymmetric Allylic Amination of Morita–Baylis–Hillman Adducts with Simple Aromatic Amines by Nucleophilic Amine Catalysis." Synlett 30, no. 06 (2019): 703–8. http://dx.doi.org/10.1055/s-0037-1611740.

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Asymmetric allylic amination of Morita–Baylis–Hillman (MBH) adducts with simple aromatic amines is successfully realized by nucleophilic amine catalysis. A range of substituted α-methylene-β-arylamino esters is accessed in moderate to high yields (up to 88%) and with excellent enantioselectivities (up to 97% ee). Inorganic fluorides are found to be able to improve the enantioselectivity of the allylic amination reaction. A pyrrole-2-carboxylate and a cyclic imide are also compatible with this catalytic system. A chiral 2,3-dihydroquinolin-4-one derivative is easily obtained from the allylic am

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10

Butcher, Trevor W., and John F. Hartwig. "Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium‐Catalyzed Allylic Fluoroalkylation." Angewandte Chemie 130, no. 40 (2018): 13309–13. http://dx.doi.org/10.1002/ange.201807474.

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11

Butcher, Trevor W., and John F. Hartwig. "Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium‐Catalyzed Allylic Fluoroalkylation." Angewandte Chemie International Edition 57, no. 40 (2018): 13125–29. http://dx.doi.org/10.1002/anie.201807474.

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12

Katcher, Matthew H., and Abigail G. Doyle. "Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides." Journal of the American Chemical Society 132, no. 49 (2010): 17402–4. http://dx.doi.org/10.1021/ja109120n.

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13

Pacheco, M. Carmen, Sophie Purser, and Véronique Gouverneur. "The Chemistry of Propargylic and Allylic Fluorides." Chemical Reviews 108, no. 6 (2008): 1943–81. http://dx.doi.org/10.1021/cr068410e.

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14

Lee, Eunsung, and Dmitry V. Yandulov. "On the isolation of neat allylic fluorides." Journal of Fluorine Chemistry 130, no. 5 (2009): 474–83. http://dx.doi.org/10.1016/j.jfluchem.2009.02.012.

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15

ERNET, T., and G. HAUFE. "ChemInform Abstract: Allylic Hydroxylation of Vinyl Fluorides." ChemInform 29, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199803070.

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16

Mixdorf, Jason C., Alexandre M. Sorlin, David W. Dick, and Hien M. Nguyen. "Iridium-Catalyzed Radiosynthesis of Branched Allylic [18F]Fluorides." Organic Letters 21, no. 1 (2018): 60–64. http://dx.doi.org/10.1021/acs.orglett.8b03496.

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17

Yin, Xuemei, Xihong Wang, Lei Song, Junxiong Zhang, and Xiaoling Wang. "Recent Progress in Synthesis of Alkyl Fluorinated Compounds with Multiple Contiguous Stereogenic Centers." Molecules 29, no. 15 (2024): 3677. http://dx.doi.org/10.3390/molecules29153677.

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Organic fluorides are widely used in pharmaceuticals, agrochemicals, material sciences, and other fields due to the special physical and chemical properties of fluorine atoms. The synthesis of alkyl fluorinated compounds bearing multiple contiguous stereogenic centers is the most challenging research area in synthetic chemistry and has received extensive attention from chemists. This review summarized the important research progress in the field over the past decade, including asymmetric electrophilic fluorination and the asymmetric elaboration of fluorinated substrates (such as allylic alkyla

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18

Madiot, Valerie, Danielle Grée, and René Grée. "A new metal mediated stereocontrolled synthesis of allylic fluorides." Tetrahedron Letters 40, no. 35 (1999): 6403–6. http://dx.doi.org/10.1016/s0040-4039(99)01330-1.

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19

Katcher, Matthew H., and Abigail G. Doyle. "ChemInform Abstract: Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides." ChemInform 42, no. 19 (2011): no. http://dx.doi.org/10.1002/chin.201119035.

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20

Greedy, Benjamin, Jean-Marc Paris, Thierry Vidal, and Véronique Gouverneur. "Regio- and Enantioselective Synthesis of Allylic Fluorides by Electrophilic Fluorodesilylation of Allyl Silanes." Angewandte Chemie International Edition 42, no. 28 (2003): 3291–94. http://dx.doi.org/10.1002/anie.200351405.

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21

Prakesch, Michaël, Danielle Grée, and René Grée. "Synthesis and reactivity of Z and E functionalized allylic fluorides." Tetrahedron 59, no. 44 (2003): 8833–41. http://dx.doi.org/10.1016/j.tet.2003.08.068.

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22

Fujita, Makoto, Hidemi Ishizuka та Katsuyuki Ogura. "Electronic effects on π-facial stereoselectivity in electrophilic additions to allylic bonds: stereoselective epoxidation of allylic fluorides". Tetrahedron Letters 32, № 44 (1991): 6355–58. http://dx.doi.org/10.1016/0040-4039(91)80168-6.

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23

Grée, Danielle, Laurent Vallerie, René Grée, et al. "Conformations of Allylic Fluorides and Stereoselectivities of Their Diels−Alder Cycloadditions." Journal of Organic Chemistry 66, no. 7 (2001): 2374–81. http://dx.doi.org/10.1021/jo0016024.

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24

Luo, Hai-Qing, and Teck-Peng Loh. "Synthesis of aryl allylic fluorides by direct electrophilic fluorination of alkenes." Tetrahedron Letters 50, no. 14 (2009): 1554–56. http://dx.doi.org/10.1016/j.tetlet.2009.01.052.

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25

Madiot, Valerie, Danielle Gree, and Rene Gree. "ChemInform Abstract: A New Metal Mediated Stereocontrolled Synthesis of Allylic Fluorides." ChemInform 30, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199945084.

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26

Mixdorf, Jason C., Alexandre M. Sorlin, Qi Zhang, and Hien M. Nguyen. "Asymmetric Synthesis of Allylic Fluorides via Fluorination of Racemic Allylic Trichloroacetimidates Catalyzed by a Chiral Diene-Iridium Complex." ACS Catalysis 8, no. 2 (2017): 790–801. http://dx.doi.org/10.1021/acscatal.7b03786.

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27

Thibaudeau, Sébastien, and Véronique Gouverneur. "Sequential Cross-Metathesis/Electrophilic Fluorodesilylation: A Novel Entry to Functionalized Allylic Fluorides." Organic Letters 5, no. 25 (2003): 4891–93. http://dx.doi.org/10.1021/ol035991a.

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28

Combettes, Lorraine E., Marie Schuler, Rakesh Patel, et al. "Synthesis of 3-Fluoropyrrolidines and 4-Fluoropyrrolidin-2-ones from Allylic Fluorides." Chemistry - A European Journal 18, no. 41 (2012): 13126–32. http://dx.doi.org/10.1002/chem.201201576.

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29

Prakesch, Michael, Danielle Grée, René Grée, Jennifer Carter, Ilyas Washington, and K. N. Houk. "Stereoselectivity of Nitrile Oxide Cycloadditions to Chiral Allylic Fluorides: Experiment and Theory." Chemistry - A European Journal 9, no. 22 (2003): 5664–72. http://dx.doi.org/10.1002/chem.200304967.

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30

FUJITA, M., H. ISHIZUKA та K. OGURA. "ChemInform Abstract: Electronic Effects on π-Facial Stereoselectivity in Electrophilic Additions to Allylic Bonds: Stereoselective Epoxidation of Allylic Fluorides." ChemInform 23, № 27 (2010): no. http://dx.doi.org/10.1002/chin.199227163.

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31

Nishimine, Takayuki, Kazunobu Fukushi, Naoyuki Shibata, et al. "Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted CF Bond Cleavage." Angewandte Chemie 126, no. 2 (2013): 527–30. http://dx.doi.org/10.1002/ange.201308071.

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32

Nishimine, Takayuki, Kazunobu Fukushi, Naoyuki Shibata, et al. "Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted CF Bond Cleavage." Angewandte Chemie International Edition 53, no. 2 (2013): 517–20. http://dx.doi.org/10.1002/anie.201308071.

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33

Kirihara, Masayuki, Toshihiro Kambayashi, and Takefumi Momose. "Allylic fluorides via the cleavage of tertiary cyclopropyl silyl ethers with diethlaminosulfur trifluoride." Chemical Communications, no. 10 (1996): 1103. http://dx.doi.org/10.1039/cc9960001103.

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34

Boldon, Sophie, Jane E. Moore, and Véronique Gouverneur. "Fluorous synthesis of allylic fluorides: C–F bond formation as the detagging process." Chemical Communications, no. 31 (2008): 3622. http://dx.doi.org/10.1039/b804484h.

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35

Wang, Zhen-Yu, Jia-Hao Wan, Gao-Yin Wang, Ruo-Xing Jin, Quan Lan, and Xi-Sheng Wang. "Nickel-Catalyzed Heck-Type Monofluoroacetation of Styrenes for Facile Synthesis of Allylic Fluorides." Chemistry - An Asian Journal 13, no. 3 (2018): 261–65. http://dx.doi.org/10.1002/asia.201701655.

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36

Jiang, Hao, Aurelia Falcicchio, Kim L. Jensen, Márcio W. Paixão, Søren Bertelsen, and Karl Anker Jørgensen. "Target-Directed Organocatalysis: A Direct Asymmetric Catalytic Approach to Chiral Propargylic and Allylic Fluorides." Journal of the American Chemical Society 131, no. 20 (2009): 7153–57. http://dx.doi.org/10.1021/ja901459z.

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37

Combettes, Lorraine E., Marie Schuler, Rakesh Patel, et al. "ChemInform Abstract: Synthesis of 3-Fluoropyrrolidines and 4-Fluoropyrrolidin-2-ones from Allylic Fluorides." ChemInform 44, no. 10 (2013): no. http://dx.doi.org/10.1002/chin.201310116.

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38

Nishimine, Takayuki, Kazunobu Fukushi, Naoyuki Shibata, et al. "ChemInform Abstract: Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted C-F Bond Cleavage." ChemInform 45, no. 30 (2014): no. http://dx.doi.org/10.1002/chin.201430051.

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39

KIRIHARA, M., T. KAMBAYASHI, and T. MOMOSE. "ChemInform Abstract: Allylic Fluorides via the Cleavage of Tertiary Cyclopropyl Silyl Ethers with Diethylaminosulfur Trifluoride." ChemInform 27, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199638088.

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40

Nishimine, Takayuki, Kazunobu Fukushi, Naoyuki Shibata, et al. "Innentitelbild: Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted CF Bond Cleavage (Angew. Chem. 2/2014)." Angewandte Chemie 126, no. 2 (2013): 340. http://dx.doi.org/10.1002/ange.201309818.

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41

Liu, Shasha, Jinbo Zhao, and Ge Zhang. "Regio- and stereoselective synthesis of functionalized allylic fluorides via palladium-catalyzed three-component tandem carbofluorination of allenes." Tetrahedron Letters 56, no. 17 (2015): 2214–18. http://dx.doi.org/10.1016/j.tetlet.2015.03.028.

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42

He, Zhi-Tao, Xingyu Jiang, and John F. Hartwig. "Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts." Journal of the American Chemical Society 141, no. 33 (2019): 13066–73. http://dx.doi.org/10.1021/jacs.9b04440.

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43

Ni, Chuanfa, and Jinbo Hu. "Fluorinative Rearrangement Involving Cleavage and Recombination of Carbon-Fluorine Bond: Synthesis of Functionalized Allylic gem-Difluorides from Propargylic Fluorides." Chinese Journal of Organic Chemistry 40, no. 9 (2020): 2997. http://dx.doi.org/10.6023/cjoc202000056.

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44

Liu, Shasha, Jinbo Zhao, and Ge Zhang. "ChemInform Abstract: Regio- and Stereoselective Synthesis of Functionalized Allylic Fluorides via Palladium-Catalyzed Three-Component Tandem Carbofluorination of Allenes." ChemInform 46, no. 33 (2015): no. http://dx.doi.org/10.1002/chin.201533052.

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45

Nishimine, Takayuki, Kazunobu Fukushi, Naoyuki Shibata, et al. "Inside Cover: Kinetic Resolution of Allyl Fluorides by Enantioselective Allylic Trifluoromethylation Based on Silicon-Assisted CF Bond CleavageZ308071 (Angew. Chem. Int. Ed. 2/2014)." Angewandte Chemie International Edition 53, no. 2 (2013): 332. http://dx.doi.org/10.1002/anie.201309818.

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46

Bernardi, Luca, Bianca F. Bonini, Mauro Comes-Franchini та ін. "First 1,3-dipolar cycloaddition of Z-α-phenyl-N-methylnitrone with allylic fluorides: a stereoselective route to enantiopure fluorine-containing isoxazolidines and amino polyols". Tetrahedron: Asymmetry 15, № 2 (2004): 245–50. http://dx.doi.org/10.1016/j.tetasy.2003.11.008.

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47

Wang, Xiaojun, and Yongming Wu. "Direct oxidative isoperfluoropropylation of terminal alkenes via hexafluoropropylene (HFP) and silver fluoride." Chemical Communications 54, no. 15 (2018): 1877–80. http://dx.doi.org/10.1039/c7cc07614b.

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Hexafluoropropylene was used directly in a reaction of copper-mediated oxidative isoperfluoropropylation of unactivated terminal alkenes. This strategy provides a general and straightforward way for the preparation of allylic isoperfluoropropylated compounds.

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48

Ranganathan, Krishnan, and Parthiban Anbanandam. "Soluble, microporous ladder polymers formed by stepwise nucleophilic substitution of octafluorocyclopentene." Polymer Chemistry 6, no. 25 (2015): 4560–64. http://dx.doi.org/10.1039/c5py00359h.

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A series of ladder polymers were prepared by reacting octafluorocyclopentene (OFCP) with various bisphenols at or above room temperature. The ladder polymers were synthesized in one or two steps with similar or different bisphenols due to different reactivities of fluorine atoms at vinylic (1,5) and (2,4) allylic positions of OFCP.

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49

Yan, Lin, Zhiqiang Han, Bo Zhu, Caiyun Yang, Choon-Hong Tan та Zhiyong Jiang. "Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters". Beilstein Journal of Organic Chemistry 9 (11 вересня 2013): 1853–57. http://dx.doi.org/10.3762/bjoc.9.216.

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In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).

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50

Hintermann, Lukas, Florian Läng, Pascal Maire та Antonio Togni. "Interactions of Cationic Palladium(II)- and Platinum(II)-η3-Allyl Complexes with Fluoride: Is Asymmetric Allylic Fluorination a Viable Reaction?" European Journal of Inorganic Chemistry 2006, № 7 (2006): 1397–412. http://dx.doi.org/10.1002/ejic.200500795.

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