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Journal articles on the topic 'Organozinc'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Chen, Yi-Hung, Mario Ellwart, Vladimir Malakhov, and Paul Knochel. "Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability." Synthesis 49, no. 15 (2017): 3215–23. http://dx.doi.org/10.1055/s-0036-1588843.

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Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture.1 Introduction2 Preparation of Organozinc Pivalates2.1 Using Organic Halides as Substrates2.2 Using a Dir

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2

Fu, Ying, Xing Ling Zhao, Hulmet Hügel, et al. "Magnesium salt promoted tandem nucleophilic addition–Oppenauer oxidation of aldehydes with organozinc reagents." Organic & Biomolecular Chemistry 14, no. 41 (2016): 9720–24. http://dx.doi.org/10.1039/c6ob01668e.

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A facile synthesis of aromatic ketones via tandem nucleophilic addition–Oppenauer oxidation of aromatic aldehydes with organozinc reagents was demonstrated. Magnesium salt in situ generated via organozinc formation is a powerful promotor for this transformation.

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3

Zemtsov, Artem A., Alexander D. Volodin, Vitalij V. Levin, Marina I. Struchkova та Alexander D. Dilman. "Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes". Beilstein Journal of Organic Chemistry 11 (10 листопада 2015): 2145–49. http://dx.doi.org/10.3762/bjoc.11.231.

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α,α-Difluoro-substituted organozinc reagents generated from conventional organozinc compounds and difluorocarbene couple with 1-bromoalkynes affording gem-difluorinated alkynes. The cross-coupling proceeds in the presence of catalytic amounts of copper iodide in dimethylformamide under ligand-free conditions.

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4

Knochel, Paul, Juan J. Almena Perea, and Philip Jones. "Organozinc mediated reactions." Tetrahedron 54, no. 29 (1998): 8275–319. http://dx.doi.org/10.1016/s0040-4020(98)00318-4.

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5

Le Gall, Erwan, Antoine Pignon, and Thierry Martens. "A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates." Beilstein Journal of Organic Chemistry 7 (July 20, 2011): 997–1002. http://dx.doi.org/10.3762/bjoc.7.112.

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A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates is described. This route involves the formation of an imine, which is used without isolation, followed by its activation by the carbonyl-containing electrophile and the trapping of the acyliminium by an organozinc reagent. Most steps are conducted concomitantly to render the procedure as practical and straightforward as possible. Therefore, the whole experimental protocol takes less than two hours.

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6

Zaragoza-Galicia, Ivann, Zaira A. Santos-Sánchez, Yazmín I. Hidalgo-Mercado, Horacio F. Olivo, and Moisés Romero-Ortega. "Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions." Synthesis 51, no. 24 (2019): 4650–56. http://dx.doi.org/10.1055/s-0037-1610733.

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A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

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7

Kim, Ju Hyun, Young Ok Ko, Jean Bouffard, and Sang-gi Lee. "Advances in tandem reactions with organozinc reagents." Chemical Society Reviews 44, no. 8 (2015): 2489–507. http://dx.doi.org/10.1039/c4cs00430b.

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8

Bellusˇ, Daniel, Bernd Klingert, Robert W. Lang, and Grety Rihs. "Fluorine-containing organozinc reagents." Journal of Organometallic Chemistry 339, no. 1-2 (1988): 17–22. http://dx.doi.org/10.1016/0022-328x(88)80520-5.

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9

Denes, Fabrice, Sabrina Cutri, Alejandro Perez-Luna, and Fabrice Chemla. "Radical-Polar Crossover Domino Reactions Involving Organozinc and Mixed Organocopper/Organozinc Reagents." Chemistry - A European Journal 12, no. 25 (2006): 6506–13. http://dx.doi.org/10.1002/chem.200600334.

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10

Kubisiak, Marcin, Karolina Zelga, Wojciech Bury, et al. "Development of zinc alkyl/air systems as radical initiators for organic reactions." Chemical Science 6, no. 5 (2015): 3102–8. http://dx.doi.org/10.1039/c5sc00600g.

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11

Fu, Ying, Yuhu Su, Qin-shan Xu, et al. "CuI promoted sulfenylation of organozinc reagents with arylsulfonyl chlorides." RSC Advances 7, no. 10 (2017): 6018–22. http://dx.doi.org/10.1039/c6ra27201k.

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12

Yang, Danfeng Huang Yihua, Jin-Xian Wang, and Yulai Hu. "Nickel (II) Catalysed 1,4- Addition Reactions of Functionalised Organozinc Reagents with Enones." Journal of Chemical Research 2002, no. 2 (2002): 79–81. http://dx.doi.org/10.3184/030823402103171339.

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13

Li, Yun, Jingchao Chen, Zhenxiu He, et al. "Cobalt-catalyzed asymmetric reactions of heterobicyclic alkenes with in situ generated organozinc halides." Organic Chemistry Frontiers 5, no. 7 (2018): 1108–12. http://dx.doi.org/10.1039/c7qo01064h.

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14

Vinogradov, Andrei S., Vyacheslav I. Krasnov, and Vyacheslav E. Platonov. "Reactions of Polyfluoroaromatic Organozinc Compounds with Acyl Chlorides and DMF." Collection of Czechoslovak Chemical Communications 73, no. 12 (2008): 1623–30. http://dx.doi.org/10.1135/cccc20081623.

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15

Murakami, Kei, and Hideki Yorimitsu. "Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation." Beilstein Journal of Organic Chemistry 9 (February 11, 2013): 278–302. http://dx.doi.org/10.3762/bjoc.9.34.

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Carbomagnesiation and carbozincation reactions are efficient and direct routes to prepare complex and stereodefined organomagnesium and organozinc reagents. However, carbon–carbon unsaturated bonds are generally unreactive toward organomagnesium and organozinc reagents. Thus, transition metals were employed to accomplish the carbometalation involving wide varieties of substrates and reagents. Recent advances of transition-metal-catalyzed carbomagnesiation and carbozincation reactions are reviewed in this article. The contents are separated into five sections: carbomagnesiation and carbozincati

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16

Casotti, Gianluca, Gianluca Ciancaleoni, Filippo Lipparini, Chiara Nieri, and Anna Iuliano. "Uncatalyzed conjugate addition of organozinc halides to enones in DME: a combined experimental/computational study on the role of the solvent and the reaction mechanism." Chemical Science 11, no. 1 (2020): 257–63. http://dx.doi.org/10.1039/c9sc04820k.

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17

Ma, Rui-Jun, Jian-Ting Sun, Chang-Hong Liu, Ling Chen, Chang-Mei Si, and Bang-Guo Wei. "Synthesis of 1-benzylisoindoline and 1-benzyl-tetrahydroisoquinoline through nucleophilic addition of organozinc reagents to N,O-acetals." Organic & Biomolecular Chemistry 18, no. 36 (2020): 7139–50. http://dx.doi.org/10.1039/d0ob01477j.

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18

Fu, Ying, Wenbo Zhu, Xingling Zhao, et al. "CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides." Org. Biomol. Chem. 12, no. 25 (2014): 4295–99. http://dx.doi.org/10.1039/c4ob00638k.

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A general and efficient CuI/TMEDA catalyzed nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides has been developed for both aromatic and aliphatic sulfone synthesis.

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19

Velarde-Ortiz, Raffet, Albert Guijarro, and Reuben D. Rieke. "Electrophilic amination of organozinc halides." Tetrahedron Letters 39, no. 50 (1998): 9157–60. http://dx.doi.org/10.1016/s0040-4039(98)02108-x.

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20

Meyer, Christophe, Ilane Marek, Gilles Courtemanche, and Jean-F. Normant. "Intramolecular carbometallation of organozinc reagents." Tetrahedron 50, no. 40 (1994): 11665–92. http://dx.doi.org/10.1016/s0040-4020(01)85661-1.

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21

KNOCHEL, P., J. J. ALMENA PEREA, and P. JONES. "ChemInform Abstract: Organozinc Mediated Reactions." ChemInform 29, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199840296.

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22

Davis, Charles R., and Donald J. Burton. "ChemInform Abstract: Fluorinated Organozinc Reagents." ChemInform 30, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199927300.

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23

Lang, Robert W., and Bruno Schaub. "Fluorine-containing organozinc reagents. IV." Tetrahedron Letters 29, no. 24 (1988): 2943–46. http://dx.doi.org/10.1016/0040-4039(88)85053-6.

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24

Greuter, Hans, Robert W. Lang, and Andres J. Romann. "Fluorine-containing organozinc reagents. V." Tetrahedron Letters 29, no. 27 (1988): 3291–94. http://dx.doi.org/10.1016/0040-4039(88)85143-8.

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25

Schulz, Stephan, and Ulrich Flörke. "Base-Stabilized Dimeric Organozinc Alkoxides." Journal of Chemical Crystallography 40, no. 10 (2010): 888–91. http://dx.doi.org/10.1007/s10870-010-9843-2.

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26

Melnik, Milan, Ján Skoršepa, Katarína Györyová, and Clive E. Holloway. "Structural analyses of organozinc compounds." Journal of Organometallic Chemistry 503, no. 1 (1995): 1–9. http://dx.doi.org/10.1016/0022-328x(95)05545-z.

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27

Galo, Cárdenas T., Oliva C. Ricardo, H. Luis, and D. Tagle. "Thermal studies of organozinc films." Thermochimica Acta 232, no. 2 (1994): 279–84. http://dx.doi.org/10.1016/0040-6031(94)80068-5.

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28

Jin, Cheng, Lijun Gu, and Minglong Yuan. "Nickel N-heterocyclic carbene-catalyzed cross-coupling reaction of aryl aldehydes with organozinc reagents to produce aryl ketones." Catalysis Science & Technology 5, no. 9 (2015): 4341–45. http://dx.doi.org/10.1039/c5cy00876j.

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The transformation of aromatic aldehydes into aryl ketones by nickel-catalyzed cross-coupling has been developed. This transformation represents an efficient and attractive synthetic utilization of organozinc reagents.

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29

Adak, Laksmikanta, Masayoshi Jin, Shota Saito, et al. "Iron-catalysed enantioselective carbometalation of azabicycloalkenes." Chemical Communications 57, no. 57 (2021): 6975–78. http://dx.doi.org/10.1039/d1cc02387j.

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The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis to in situ form optically active organozinc intermediates, which are amenable to further synthetic elaborations.

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30

Echavarren, Javier, Malcolm A. Y. Gall, Adrian Haertsch, David A. Leigh, Vanesa Marcos, and Daniel J. Tetlow. "Active template rotaxane synthesis through the Ni-catalyzed cross-coupling of alkylzinc reagents with redox-active esters." Chemical Science 10, no. 30 (2019): 7269–73. http://dx.doi.org/10.1039/c9sc02457c.

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31

Allef, Petra, та Horst Kunz. "Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-induced Asymmetric Addition of Organometallic Compounds to Imines". Zeitschrift für Naturforschung B 64, № 6 (2009): 646–52. http://dx.doi.org/10.1515/znb-2009-0609.

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Activation of imines of aromatic aldehydes by N-glycosylation with O-pivaloyl-galactopyranosyl bromide (pivalobromogalactose) and subsequent addition of organotin, organolithium, Grignard, or organozinc reagents afforded α-arylalkylamines with moderate to high diastereoselectivity.

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32

Naganawa, Yuki, Tomoya Namba, Tomotaka Aoyama, Kentaro Shoji, and Hisao Nishiyama. "Design of novel chiral N,N,O-tridentate phenanthroline ligands and their application to enantioselective addition of organozinc reagents to aldehydes." Chem. Commun. 50, no. 87 (2014): 13224–27. http://dx.doi.org/10.1039/c4cc05020g.

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The novel chiral N,N,O-tridentate ligands (BinThro) containing binaphthyl and phenanthroline units were developed. The enantioselective organozinc addition to aldehydes was performed in the presence of BinThro (S)-1 with up to 95% ee.

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33

Das, Pragna Pratic, Bibhuti Bhusan Parida, and Jin Kun Cha. "Organozinc-promoted ring opening of cyclopropanols." Arkivoc 2012, no. 2 (2012): 74–84. http://dx.doi.org/10.3998/ark.5550190.0013.208.

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34

Barwick, Mat, Tareq Abu-Izneid, Igor Novak, and Branka Kovač. "Photoelectron spectra of some organozinc compounds." Chemical Physics Letters 460, no. 1-3 (2008): 79–81. http://dx.doi.org/10.1016/j.cplett.2008.06.029.

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35

Meyer, Christophe, Ilane Marek, Gilles Courtemanche, and Jean-F. Normant. "Intramolecular carbometallation of secondary organozinc reagents." Tetrahedron Letters 34, no. 38 (1993): 6053–56. http://dx.doi.org/10.1016/s0040-4039(00)61725-2.

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36

Haag, Benjamin A., Zhi-Guang Zhang, Jin-Shan Li, and Paul Knochel. "Fischer Indole Synthesis with Organozinc Reagents." Angewandte Chemie International Edition 49, no. 49 (2010): 9513–16. http://dx.doi.org/10.1002/anie.201005319.

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37

Teunissen, Herman T., and Friedrich Bickelhaupt. "Reactivity of Organozinc Derivatives of Phosphinines." Organometallics 15, no. 2 (1996): 802–8. http://dx.doi.org/10.1021/om9506936.

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38

Su, Xianbin, David J. Fox, David T. Blackwell, Kiyotaka Tanaka, and David R. Spring. "Copper catalyzed oxidation of organozinc halides." Chemical Communications, no. 37 (2006): 3883. http://dx.doi.org/10.1039/b610218b.

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39

Levin, Vitalij V., Artem A. Zemtsov, Marina I. Struchkova, and Alexander D. Dilman. "Reactions of Difluorocarbene with Organozinc Reagents." Organic Letters 15, no. 4 (2013): 917–19. http://dx.doi.org/10.1021/ol400122k.

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40

Bollermann, Timo, Christian Gemel, and Roland A. Fischer. "Organozinc ligands in transition metal chemistry." Coordination Chemistry Reviews 256, no. 5-8 (2012): 537–55. http://dx.doi.org/10.1016/j.ccr.2011.11.008.

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41

Zheng, Songlin, та Songlin Zhang. "Synthesis of allyl-aziridines from α-halo oxime ethers and allyl zinc bromides". RSC Advances 6, № 31 (2016): 26437–40. http://dx.doi.org/10.1039/c5ra26394h.

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A novel method for the preparation of allyl aziridines by reacting α-halo oxime ethers with allylic zinc reagents under mild conditions. Some advantages of using organozinc reagents are that they are easily prepared, non-toxic, and more selective than Grignard reagents.

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42

Nikitin, Kirill V., and Nonna P. Andryukhova. "Synthesis of 5-alkyl- and 5-aryl-1,5-dihydro-2H-pyrrol-2-ones via coupling of 5-chloro-1,5-dihydro-2H-pyrrol-2-ones with organometallic compounds." Canadian Journal of Chemistry 78, no. 10 (2000): 1285–88. http://dx.doi.org/10.1139/v00-127.

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5-Chloro-1,5-dihydro-2H-pyrrol-2-ones are easily alkylated at the 5-position by organomagnesium or organozinc compounds and diethyl sodiomalonate leading to corresponding 5-alkyl-1,5-dihydro-2H-pyrrol-2-ones in high yields.Key words: organometallic compounds, alkylation, 1,5-dihydro-2H-pyrrol-2-one.

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43

De Munck, Lode, Carlos Vila, Carolina Pons та José Pedro. "Synthesis of Multisubstituted 1,4-Dihydrobenzoxazin-2-ones through a One-Pot Nucleophilic N-Alkylation/C-Alkylation of Cyclic α-Imino Esters". Synthesis 49, № 12 (2017): 2683–90. http://dx.doi.org/10.1055/s-0036-1588742.

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A nucleophilic N-alkylation of 2-oxobenzoxazine-2-carboxylates with organozinc reagents with good selectivities and in moderate to good yields is described. Moreover, the synthesis of multisubstituted 1,4-dihydrobenzoxazine-2-ones bearing a tetrasubstituted carbon atom via a one-pot N-alkylation/C-alkylation reactions is reported.

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44

Ellwart, Mario, Georg Höfner, Aaron Gerwien, Klaus Wanner, and Paul Knochel. "Synthesis and Bioactivity of Novel N-Benzylic and N-Phenethylic Ephedrine Derivatives." Synthesis 49, no. 23 (2017): 5159–66. http://dx.doi.org/10.1055/s-0036-1588523.

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A range of N-benzylic and N-phenethylic ephedrine derivatives were prepared in a one-pot procedure starting from the two enantiomers of ephedrine using the Potier reagent, and a polyfunctional aryl- or benzylic organozinc halide. The biological activity in indatraline MS Binding Assays addressing hDAT, hNET and hSERT was determined and discussed.

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45

Motherwell, William B. "Curiosity and simplicity in the invention and discovery of new metal-mediated reactions for organic synthesis." Pure and Applied Chemistry 74, no. 1 (2002): 135–42. http://dx.doi.org/10.1351/pac200274010135.

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Two organometallic themes of current interest are presented. The scope and generality of the reductive deoxygenation of carbonyl compounds to organozinc carbenoids using zinc in combination with a silicon electrophile is discussed. Alkoxycyclopropanation can be achieved using orthoformates as substrates. Preliminary observations on the development of a rhodium-catalyzed tandem hydrosilylationintramolecular aldol sequence are discussed.

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46

Dilman, Alexander, Vitalij Levin, Daniil Agababyan, and Marina Struchkova. "Dimerization of Benzyl and Allyl Halides via Photoredox-Mediated Disproportionation of Organozinc Reagents." Synthesis 50, no. 15 (2018): 2930–35. http://dx.doi.org/10.1055/s-0036-1591583.

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Benzyl and allyl halides undergo homocoupling when treated with zinc in the presence of a catalytic amount of a cationic iridium(III) complex under irradiation with 400 nm light-emitting diodes. The reaction proceeds through the intermediate formation of an organozinc reagent, which disproportionates to a free radical and elemental zinc under photoredox conditions.

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47

Erdik, Ender. "Transition metal catalyzed reactions of organozinc reagents." Tetrahedron 48, no. 44 (1992): 9577–648. http://dx.doi.org/10.1016/s0040-4020(01)81181-9.

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48

Pu, Lin, and Hong-Bin Yu. "Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds." Chemical Reviews 101, no. 3 (2001): 757–824. http://dx.doi.org/10.1021/cr000411y.

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49

Yang, Haoran, Danfeng Huang, Ke-Hu Wang, Changming Xu, Teng Niu, and Yulai Hu. "Reaction of organozinc halides with aryl isocyanates." Tetrahedron 69, no. 12 (2013): 2588–93. http://dx.doi.org/10.1016/j.tet.2013.01.053.

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50

Klement, Ingo, Henning Lütjens, and Paul Knochel. "Chemoselective oxidation of organozinc reagents with oxygen." Tetrahedron 53, no. 27 (1997): 9135–44. http://dx.doi.org/10.1016/s0040-4020(97)00603-0.

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