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Journal articles on the topic 'Grignard reagents. Halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Yorimitsu, Hideki, and Koichiro Oshima. "New synthetic reactions catalyzed by cobalt complexes." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 441–49. http://dx.doi.org/10.1351/pac200678020441.

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Without suffering from β-elimination, cobalt complexes allow cross-coupling reactions of alkyl halides with Grignard reagents. A combination of a cobalt complex and trimethylsilylmethyl Grignard reagent effects Mizoroki-Heck-type reaction of alkyl halide with styrene, which conventional palladium catalysts have never made possible. Cobalt exhibits intriguing catalytic activities on hydrophosphination and allylzincation of alkynes. Silylmethylcobalt reagent is a powerful tool for the synthesis of highly silylated ethenes.

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2

Dai, Zhi Qun, Zhi Yong Zhang, Wei Wei Zhang, and Ben Mei Wei. "Cross-coupling Reaction of Grignard Reagents with Alkyl Halides Catalyzed by Green, Economical Copper Bromide Catalyst." Advanced Materials Research 233-235 (May 2011): 1119–22. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.1119.

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For the first time a systematic research on the catalytic activity of CuXn(X=Cl, Br, I; x=1,2) for the cross-coupling reaction of alkyl halides with Grignard reagents was carried out and environmentally friendly, economical CuBr2showed highest catalytic activity among the catalyst. The conditions of the cross-coupling reaction were studied. The suitable amount of catalyst, reaction temperature and time are 0.3% mol (based on alkyl halide), 67°C (reflux), 6 h, respectively. Under the optimal conditions, the yields of the cross-coupling could reach up to 93%. Moreover, Grignard reagent with an electron-rich group reacted rapidly and with an electron-withdrawing group reacted sluggishly.

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3

Clark, Peter D., Russell S. Mann, and Kevin L. Lesage. "Reactions of dimethyl polysulfides with organomagnesium reagents." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 29–33. http://dx.doi.org/10.1139/v92-006.

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Reactions of a mixture of dimethyl polysulfides (DMPS, CH3SxCH3, x = 3 – 8) with methyl- and phenylmagnesium halides are described. The type of product obtained was dependent on the molar ratio of DMPS to Grignard reagent. When a 6:1 methyl-Grignard to DMPS ratio was used, methanethiol and dimethyl sulfide were the major products obtained after acidification of the reaction mixture. Lesser quantities of methyl-Grignard favored the formation of dimethyl sulfide, dimethyl disulfide, and H2S. Experiments with a 6:1 phenylmagnesium bromide to DMPS ratio produced benzenethiol and phenylmethyl sulfide as major products after acidification. No methanethiol was observed in these experiments. Mixtures of phenylmethyl mono-, di-, and trisulfides and H2S were obtained with a 3:1 Grignard/DMPS molar ratio. From a mechanistic viewpoint, product distributions obtained from reaction of Grignard reagents with DMPS can be explained by the formation of magnesium thiolates that are most readily stabilized by adjacent structures. Experiments using phenyl Grignard reagent in limited supply suggested that the internal sulfur atoms of the polysulfide chains were most reactive. Keywords: organic polysulfides, Grignard reagents.

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4

Kabalka, G. W., Z. Wu, and Y. Ju. "Use of organoboron halides in organic synthesis." Pure and Applied Chemistry 75, no. 9 (January 1, 2003): 1231–37. http://dx.doi.org/10.1351/pac200375091231.

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Several new organic transformations have been achieved utilizing boron halide reagents. Aryl aldehydes are conveniently converted to gem-dichloromethylbenzenes using boron trichloride. Aryl aldehydes are alkylated by alkylboron chlorides in a Grignard-like fashion to generate the corresponding arylalkanols or alkylboron chlorides. Aryl aldehydes react with divinylboron halides (generated via the haloboration of alkynes) to produce 1,5-di-halo-1,4-dienes in excellent yields.

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5

Xu, Lijun, Zhubo Liu, Weipeng Dong, Jinyu Song, Maozhong Miao, Jianfeng Xu, and Hongjun Ren. "Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents." Organic & Biomolecular Chemistry 13, no. 22 (2015): 6333–37. http://dx.doi.org/10.1039/c5ob00594a.

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6

Liu, Lei, Wes Lee, Cassandra R. Youshaw, Mingbin Yuan, Michael B. Geherty, Peter Y. Zavalij, and Osvaldo Gutierrez. "Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents." Chemical Science 11, no. 31 (2020): 8301–5. http://dx.doi.org/10.1039/d0sc02127j.

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7

Liu, Lei, Wes Lee, Mingbin Yuan, Chris Acha, Michael B. Geherty, Brandon Williams, and Osvaldo Gutierrez. "Intra- and intermolecular Fe-catalyzed dicarbofunctionalization of vinyl cyclopropanes." Chemical Science 11, no. 12 (2020): 3146–51. http://dx.doi.org/10.1039/d0sc00467g.

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Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach.

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8

Best, Wayne M., Vito Ferro, Julia Harle, Robert V. Stick, and D. Matthew G. Tilbrook. "The Synthesis of Some Epoxyalkyl b-C-Glycosides as Potential Inhibitors of b-Glucan Hydrolases." Australian Journal of Chemistry 50, no. 5 (1997): 463. http://dx.doi.org/10.1071/c97015.

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The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-β-D-C-glucopyranosides in good yield. These β-D-C-glucosides were precursors of the epoxyalkyl β-D-C-glucopyranosides, themselves putative inhibitors of b-glucan hydrolases. Similar additions of Grignard reagents to per-benzylated cellobionolactone were not as successful in yielding epoxyalkyl β-C-cellobiosides. The addition of Grignard reagents to 1,2-anhydro-3,4,6-tri-O-benzyl-α-D- glucose offers a viable alternative route to the prop-2-enyl β-D-C-glucoside, but not to the but-3-enyl and pent-4-enyl counterparts. Likewise, the addition of Grignard reagents to a 1,2-anhydro cellobiose gave disappointing results. Preliminary results are reported for a novel approach to alkenyl β-D-C-glucosides by the alkylation of nitromethyl β-D-C-glucosides.

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9

Quintin, Jérôme, Xavier Franck, Reynald Hocquemiller, and Bruno Figadère. "Iron-catalysed arylation of heteroaryl halides by Grignard reagents." Tetrahedron Letters 43, no. 19 (May 2002): 3547–49. http://dx.doi.org/10.1016/s0040-4039(02)00568-3.

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10

Guérinot, Amandine, and Janine Cossy. "Cobalt-Catalyzed Cross-Couplings between Alkyl Halides and Grignard Reagents." Accounts of Chemical Research 53, no. 7 (July 10, 2020): 1351–63. http://dx.doi.org/10.1021/acs.accounts.0c00238.

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11

Sai, Masahiro, Hideki Yorimitsu, and Koichiro Oshima. "Copper-Catalyzed Allylation of Alkyl Halides with Allylic Grignard Reagents." Bulletin of the Chemical Society of Japan 82, no. 9 (September 15, 2009): 1194–96. http://dx.doi.org/10.1246/bcsj.82.1194.

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12

Terao, J., N. Kambe, H. Todo, S. Begum, and H. Kuniyasu. "Cu-Catalyzed Coupling of Grignard Reagents with Primary Alkyl Halides." Synfacts 2007, no. 5 (May 2007): 0536. http://dx.doi.org/10.1055/s-2007-968423.

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13

Luo, Meiming, Xiaoming Zeng, and Jinghua Tang. "Chromium-Catalyzed, Regioselective Cross-Coupling of C–O Bonds by Using Organic Bromides as Reactants." Synlett 28, no. 19 (September 14, 2017): 2577–80. http://dx.doi.org/10.1055/s-0036-1588568.

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We report a chromium-catalyzed cross-coupling of C–O bonds with widely accessible organic bromides as reactants for the preparation of ortho-arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

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14

Tsuji, Takashi, Hideki Yorimitsu, and Koichiro Oshima. "Cobalt-Catalyzed Coupling Reaction of Alkyl Halides with Allylic Grignard Reagents." Angewandte Chemie International Edition 41, no. 21 (November 4, 2002): 4137–39. http://dx.doi.org/10.1002/1521-3773(20021104)41:21<4137::aid-anie4137>3.0.co;2-0.

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15

Guérinot, Amandine, Sébastien Reymond, and Janine Cossy. "Iron-Catalyzed Cross-Coupling of Alkyl Halides with Alkenyl Grignard Reagents." Angewandte Chemie 119, no. 34 (August 27, 2007): 6641–44. http://dx.doi.org/10.1002/ange.200702206.

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16

Quintin, Jerome, Xavier Franck, Reynald Hocquemiller, and Bruno Figadere. "ChemInform Abstract: Iron-Catalyzed Arylation of Heteroaryl Halides by Grignard Reagents." ChemInform 33, no. 34 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200234080.

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17

Guérinot, Amandine, Sébastien Reymond, and Janine Cossy. "Iron-Catalyzed Cross-Coupling of Alkyl Halides with Alkenyl Grignard Reagents." Angewandte Chemie International Edition 46, no. 34 (August 27, 2007): 6521–24. http://dx.doi.org/10.1002/anie.200702206.

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18

Kim, Ju Hyun, and Young Keun Chung. "Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents." Chemical Communications 49, no. 94 (2013): 11101. http://dx.doi.org/10.1039/c3cc46419a.

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19

Fleury, Lauren M., and Brandon L. Ashfeld. "Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides." Tetrahedron Letters 51, no. 18 (May 2010): 2427–30. http://dx.doi.org/10.1016/j.tetlet.2010.02.144.

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20

Kambe, Nobuaki, Yuusuke Moriwaki, Yuuki Fujii, Takanori Iwasaki, and Jun Terao. "Silver-Catalyzed Regioselective Carbomagnesiation of Alkynes with Alkyl Halides and Grignard Reagents." Organic Letters 13, no. 17 (September 2, 2011): 4656–59. http://dx.doi.org/10.1021/ol2018664.

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21

Andersen, Claire, Vincent Ferey, Marc Daumas, Patrick Bernardelli, Amandine Guérinot, and Janine Cossy. "Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents." Organic Letters 22, no. 15 (July 16, 2020): 6021–25. http://dx.doi.org/10.1021/acs.orglett.0c02115.

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22

Yasuda, Shigeo, Hideki Yorimitsu, and Koichiro Oshima. "Vanadium-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents." Bulletin of the Chemical Society of Japan 81, no. 2 (February 15, 2008): 287–90. http://dx.doi.org/10.1246/bcsj.81.287.

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23

Bedford, Robin B., Michael Betham, Duncan W. Bruce, Sean A. Davis, Robert M. Frost, and Michael Hird. "Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents." Chemical Communications, no. 13 (2006): 1398. http://dx.doi.org/10.1039/b601014h.

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24

Cahiez, Gérard, Olivier Gager, and Fabien Lecomte. "Manganese-Catalyzed Cross-Coupling Reaction between Aryl Grignard Reagents and Alkenyl Halides." Organic Letters 10, no. 22 (November 20, 2008): 5255–56. http://dx.doi.org/10.1021/ol802273e.

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25

Gazzola, Silvia, Malcolm R. Gordon, and Stephen D. Lindell. "General Route to Purin-2-ylmagnesium Halides by Metal–Halogen Exchange in Dichloromethane." Synlett 31, no. 05 (February 10, 2020): 512–16. http://dx.doi.org/10.1055/s-0039-1690818.

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Treatment of a solution of a 9-alkyl- or 9-aryl-2-iodopurine in dichloromethane with an ethereal solution of ethylmagnesium bromide at –5 °C generates the corresponding purin-2-ylmagnesium bromide, which reacts with aldehydes to give the corresponding 2-(hydroxyalkyl)purines in yields of 53–84%. The purin-2-yl Grignard reagents show good functional-group tolerance to ester and nitro groups, and the method permits the synthesis of the previously unknown 6-unsubstituted 2-magnesiopurines for the first time. Performing the same procedure in THF as solvent resulted either in extensive decomposition or rapid isomerization to give purin-8-ylmagnesium halides.

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26

Shimotori, Yasutaka, Masayuki Hoshi, Keita Inoue, Takeshi Osanai, Hayato Okabe, and Tetsuo Miyakoshi. "Preparation of optically active 4-substituted γ-lactones by lipase-catalyzed optical resolution." Heterocyclic Communications 21, no. 3 (June 1, 2015): 165–74. http://dx.doi.org/10.1515/hc-2015-0027.

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AbstractOptically active 4-substituted γ-lactones (3 and 4) were synthesized effectively using lipase-catalyzed optical resolution. N-methyl-4-hydroxyalkanamides (rac-1a–i) as substrates were prepared from N-methylsuccinimide. The alkylation of N-methylsuccinimide using Grignard reagents generated from various alkyl halides followed by reduction resulted in N-methyl-4-hydroxyalkanamides. The optical resolution of rac-1a–g was performed using Novozym 435-catalyzed stereoselective acetylation. The stereoselective preparation of 4-substituted γ-lactones (3 and 4) possessing various side chains such as isopentyl, phenyl, and phenethyl groups was achieved with more than 90% enantiopurity.

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27

Kim, Ju Hyun, and Young Keun Chung. "ChemInform Abstract: Copper Nanoparticle-Catalyzed Cross-Coupling of Alkyl Halides with Grignard Reagents." ChemInform 45, no. 13 (March 14, 2014): no. http://dx.doi.org/10.1002/chin.201413043.

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28

Le Bailly, Bryden A. F., Mark D. Greenhalgh, and Stephen P. Thomas. "Iron-catalysed, hydride-mediated reductive cross-coupling of vinyl halides and Grignard reagents." Chem. Commun. 48, no. 10 (2012): 1580–82. http://dx.doi.org/10.1039/c1cc14622j.

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29

Cahiez, Gérard, Olivier Gager, Julien Buendia, and Cindy Patinote. "Iron Thiolate Complexes: Efficient Catalysts for Coupling Alkenyl Halides with Alkyl Grignard Reagents." Chemistry - A European Journal 18, no. 19 (March 29, 2012): 5860–63. http://dx.doi.org/10.1002/chem.201200184.

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30

Cahiez, Gérard, Olivier Gager, and Julien Buendia. "Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides." Angewandte Chemie International Edition 49, no. 7 (January 8, 2010): 1278–81. http://dx.doi.org/10.1002/anie.200905816.

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31

Cahiez, Gérard, Olivier Gager, and Julien Buendia. "Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides." Angewandte Chemie 122, no. 7 (February 8, 2010): 1300–1303. http://dx.doi.org/10.1002/ange.200905816.

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32

Ikoma, Yoshiharu, Fumio Taya, Ei-ichi Ozaki, Shigeki Higuchi, Yoshitake Naoi, and Kiyomi Fuji-i. "Non-ligated Nickel Chloride-Catalyzed Cross-Coupling of Aromatic Grignard Reagents with Aryl Halides." Synthesis 1990, no. 02 (1990): 147–48. http://dx.doi.org/10.1055/s-1990-26816.

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33

Nakamura, Masaharu, Keiko Matsuo, Shingo Ito, and Eiichi Nakamura. "Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents." Journal of the American Chemical Society 126, no. 12 (March 2004): 3686–87. http://dx.doi.org/10.1021/ja049744t.

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34

Dongol, Krishna G, Huishi Koh, Manisankar Sau, and Christina L. L. Chai. "Iron-Catalysedsp3–sp3 Cross-Coupling Reactions of Unactivated Alkyl Halides with Alkyl Grignard Reagents." Advanced Synthesis & Catalysis 349, no. 7 (May 7, 2007): 1015–18. http://dx.doi.org/10.1002/adsc.200600383.

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35

Kambe, Nobuaki, Yuusuke Moriwaki, Yuuki Fujii, Takanori Iwasaki, and Jun Terao. "ChemInform Abstract: Silver-Catalyzed Regioselective Carbomagnesiation of Alkynes with Alkyl Halides and Grignard Reagents." ChemInform 43, no. 2 (December 15, 2011): no. http://dx.doi.org/10.1002/chin.201202046.

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36

Hedström, Anna, Ulla Bollmann, Jenny Bravidor, and Per-Ola Norrby. "Iron-Catalyzed Coupling of Aryl Grignard Reagents with Alkyl Halides: A Competitive Hammett Study." Chemistry - A European Journal 17, no. 43 (September 16, 2011): 11991–93. http://dx.doi.org/10.1002/chem.201100467.

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37

Fleury, Lauren M., and Brandon L. Ashfeld. "ChemInform Abstract: Generation of Allyl Grignard Reagents via Titanocene-Catalyzed Activation of Allyl Halides." ChemInform 41, no. 34 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034072.

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38

Antonacci, Giuseppe, Andreas Ahlburg, Peter Fristrup, Per-Ola Norrby, and Robert Madsen. "Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism." European Journal of Organic Chemistry 2017, no. 32 (August 25, 2017): 4758–64. http://dx.doi.org/10.1002/ejoc.201700981.

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39

Shirakawa, Eiji, Ryo Watabe, Takuya Murakami, and Tamio Hayashi. "Single electron transfer-induced cross-coupling reaction of alkenyl halides with aryl Grignard reagents." Chemical Communications 49, no. 45 (2013): 5219. http://dx.doi.org/10.1039/c3cc41923a.

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40

Cahiez, Gerard, Olivier Gager, and Julien Buendia. "ChemInform Abstract: Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides." ChemInform 41, no. 24 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.201024060.

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41

Vechorkin, Oleg, and Xile Hu. "Nickel-Catalyzed Cross-Coupling of Non-activated and Functionalized Alkyl Halides with Alkyl Grignard Reagents." Angewandte Chemie International Edition 48, no. 16 (January 28, 2009): 2937–40. http://dx.doi.org/10.1002/anie.200806138.

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42

Xie, Lan-Gui, and Zhong-Xia Wang. "Nickel-Catalyzed Cross-Coupling of Non-Activated or Functionalized Aryl Halides with Aryl Grignard Reagents." Chemistry - A European Journal 16, no. 34 (July 20, 2010): 10332–36. http://dx.doi.org/10.1002/chem.201001022.

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43

Vechorkin, Oleg, and Xile Hu. "Nickel-Catalyzed Cross-Coupling of Non-activated and Functionalized Alkyl Halides with Alkyl Grignard Reagents." Angewandte Chemie 121, no. 16 (January 28, 2009): 2981–84. http://dx.doi.org/10.1002/ange.200806138.

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44

Le Bailly, Bryden A. F., Mark D. Greenhalgh, and Stephen P. Thomas. "ChemInform Abstract: Iron-Catalyzed, Hydride-Mediated Reductive Cross-Coupling of Vinyl Halides and Grignard Reagents." ChemInform 43, no. 26 (May 31, 2012): no. http://dx.doi.org/10.1002/chin.201226050.

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45

Cahiez, Gerard, Olivier Gager, Julien Buendia, and Cindy Patinote. "ChemInform Abstract: Iron Thiolate Complexes: Efficient Catalysts for Coupling Alkenyl Halides with Alkyl Grignard Reagents." ChemInform 43, no. 35 (August 2, 2012): no. http://dx.doi.org/10.1002/chin.201235038.

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46

Someya, Hidenori, Hirohisa Ohmiya, Hideki Yorimitsu, and Koichiro Oshima. "Silver-Catalyzed Benzylation and Allylation Reactions of Tertiary and Secondary Alkyl Halides with Grignard Reagents." Organic Letters 10, no. 5 (March 2008): 969–71. http://dx.doi.org/10.1021/ol800038a.

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47

Murahashi, Shun-Ichi. "Palladium-catalyzed cross-coupling reaction of organic halides with Grignard reagents, organolithium compounds and heteroatom nucleophiles." Journal of Organometallic Chemistry 653, no. 1-2 (July 2002): 27–33. http://dx.doi.org/10.1016/s0022-328x(02)01167-1.

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48

Chard, Elliott F., Louise N. Dawe, and Christopher M. Kozak. "Coupling of benzyl halides with aryl Grignard reagents catalyzed by iron(III) amine-bis(phenolate) complexes." Journal of Organometallic Chemistry 737 (August 2013): 32–39. http://dx.doi.org/10.1016/j.jorganchem.2013.03.034.

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49

Wang, Lei, Xiaofang Chen, and Jie Liu. "Kumada Cross-Coupling of Aryl Grignard Reagents with Aryl Halides Catalyzed by an Immobilized Nickel Catalyst." Synthesis 2009, no. 14 (May 27, 2009): 2408–12. http://dx.doi.org/10.1055/s-0029-1216832.

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50

Nakata, Kenya, Chao Feng, Toshifumi Tojo, and Yuichi Kobayashi. "Acceleration of CuI-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents using lithium chloride." Tetrahedron Letters 55, no. 42 (October 2014): 5774–77. http://dx.doi.org/10.1016/j.tetlet.2014.08.089.

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