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Journal articles on the topic 'Vinyl Grignard Reagents'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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1

Dörr, Aurélie A., and William D. Lubell. "Homoallylic ketones and pyrroles by way of copper-catalyzed cascade additions of alkyl-substituted vinyl Grignard reagents to esters." Canadian Journal of Chemistry 85, no. 11 (2007): 1006–17. http://dx.doi.org/10.1139/v07-114.

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Exploring the scope of the copper-catalyzed cascade addition of vinyl Grignard reagents to carboxylic esters, a set of substituted homoallylic ketones (γ,δ-unsaturated ketones) have been synthesized in 11%–94% yields from treatment of methyl 4-methoxybenzoate and methyl N-Boc-β-alaninate with different methyl-, dimethyl-, and phenyl-substituted vinyl Grignard reagents in the presence of catalytic amounts of CuCN in THF. The respective 2,4-di-, 2,3,5-tri-, and 2,3,4,5-tetrasubstituted pyrroles were obtained in 47%–93% yields from the homoallylic ketones by a sequence featuring ozonolysis follow

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2

Lin, Zhu, De-Hua Zhai, Yong-Ming Sun, et al. "Tandem addition of nucleophilic and electrophilic reagents to vinyl phosphinates: the stereoselective formation of organophosphorus compounds with congested tertiary carbons." RSC Advances 13, no. 21 (2023): 14060–64. http://dx.doi.org/10.1039/d3ra02409a.

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3

Liu, Lei, Wes Lee, Mingbin Yuan, et al. "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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4

Parmar, Dixit, Lena Henkel, Josef Dib, and Magnus Rueping. "Iron catalysed cross-couplings of azetidines – application to the formal synthesis of a pharmacologically active molecule." Chemical Communications 51, no. 11 (2015): 2111–13. http://dx.doi.org/10.1039/c4cc09337b.

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A protocol for the cross-coupling of azetidines with aryl, heteroaryl, vinyl and alkyl Grignard reagents has been developed under iron catalysis. In addition, a short formal synthesis of a pharmacologically active molecule was demonstrated.

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5

Sherry, Benjamin D., and Alois Fürstner. "Iron-catalyzed addition of Grignard reagents to activated vinyl cyclopropanes." Chemical Communications, no. 46 (2009): 7116. http://dx.doi.org/10.1039/b918818e.

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6

Mahfouz, Nadine, Fatima Abi-Ghaida, Wael Kotob, Ahmad Mehdi, and Daoud Naoufal. "Selective Functionalization of Carbonyl Closo-Decaborate [2-B10H9CO]− with Building Block Properties via Grignard Reagents." Molecules 28, no. 16 (2023): 6076. http://dx.doi.org/10.3390/molecules28166076.

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A green, fast and selective approach for the synthesis of mono-substituted closo-decaborate derivatives [2-B10H9COR]2− has been established via a nucleophilic addition reaction between the carbonyl derivative of closo-decaborate [2-B10H9CO]− and the corresponding Grignard reagent RMgX, where R is the ethyl, iso-propyl, pentyl, allyl, vinyl and propynyl groups. This approach is accomplished under mild conditions with 70–80% yields. The significance of these derivative is their ability to constitute building blocks for polymeric integration via the allyl, vinyl and propynyl substituents. All pro

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7

Terao, Jun, Hiroyasu Watabe, and Nobuaki Kambe. "Ni-Catalyzed Alkylative Dimerization of Vinyl Grignard Reagents Using Alkyl Fluorides." Journal of the American Chemical Society 127, no. 11 (2005): 3656–57. http://dx.doi.org/10.1021/ja042565r.

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8

Wang, Z. "C–H activation by Grignard reagents: vinyl plus methylene coupling on iridium." Journal of Organometallic Chemistry 569, no. 1-2 (1998): 85–88. http://dx.doi.org/10.1016/s0022-328x(98)00776-1.

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9

Hirai, Atsushi, Masaharu Nakamura, and Eiichi Nakamura. "Synergetic Dimetallic Effects in Gaudemar/Normant Coupling between Allylzinc and Vinyl Grignard Reagents." Journal of the American Chemical Society 121, no. 37 (1999): 8665–66. http://dx.doi.org/10.1021/ja9914590.

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10

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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11

Bosco, Marcella, Renato Dalpozzo, Giuseppe Bartoli, Gianni Palmieri, and Marino Petrini. "Mechanistic studies on the reaction of nitro- and nitrosoarenes with vinyl Grignard reagents." Journal of the Chemical Society, Perkin Transactions 2, no. 5 (1991): 657. http://dx.doi.org/10.1039/p29910000657.

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12

Iwasaki, Takanori, Yoshinori Miyata, Ryo Akimoto, Yuuki Fujii, Hitoshi Kuniyasu, and Nobuaki Kambe. "Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents." Journal of the American Chemical Society 136, no. 26 (2014): 9260–63. http://dx.doi.org/10.1021/ja5043534.

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13

Busacca, Carl A., Magnus C. Eriksson, and Rita Fiaschi. "Cross coupling of vinyl triflates and alkyl Grignard reagents catalyzed by nickel(0)-complexes." Tetrahedron Letters 40, no. 16 (1999): 3101–4. http://dx.doi.org/10.1016/s0040-4039(99)00439-6.

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14

Gomtsyan, Arthur, Robert J. Koenig та Chih-Hung Lee. "Novel Sequential Process fromN-Methoxyamides and Vinyl Grignard Reagents: New Synthesis of β-Aminoketones." Journal of Organic Chemistry 66, № 21 (2001): 7235. http://dx.doi.org/10.1021/jo0129475.

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15

Gomtsyan, Arthur, Robert J. Koenig та Chih-Hung Lee. "Novel Sequential Process fromN-Methoxyamides and Vinyl Grignard Reagents: New Synthesis of β-Aminoketones". Journal of Organic Chemistry 66, № 10 (2001): 3613–16. http://dx.doi.org/10.1021/jo0057497.

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16

Boga, Carla, Luciano Forlani, and Paolo E. Todesco. "Unexpected regioselectivity in the attack of vinyl Grignard reagents to bis(2-benzothiazolyl) ketone." Tetrahedron Letters 38, no. 27 (1997): 4845–48. http://dx.doi.org/10.1016/s0040-4039(97)01009-5.

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17

Nishiyama, Tomihiro, Takeshi Seshita, Hiroshi Shodai, Kazushige Aoki, Hideaki Kameyama, and Kenichi Komura. "New Homo-coupling Reaction of Alkyl, Aryl, Vinyl, and Allyl Grignard Reagents Using Trifluoromethanesulfonic Anhydride." Chemistry Letters 25, no. 7 (1996): 549–50. http://dx.doi.org/10.1246/cl.1996.549.

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18

Bartoli, Giuseppe, Marcella Bosco, Renato Dalpozzo, Gianni Palmieri, and Enrico Marcantoni. "Reactivity of nitro- and nitroso-arenes with vinyl grignard reagents: synthesis of 2-(trimethylsilyl)indoles." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (1991): 2757. http://dx.doi.org/10.1039/p19910002757.

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19

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 (2012): no. http://dx.doi.org/10.1002/chin.201226050.

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20

BOSCO, M., R. DALPOZZO, G. BARTOLI, G. PALMIERI, and M. PETRINI. "ChemInform Abstract: Mechanistic Studies on the Reaction of Nitro- and Nitrosoarenes with Vinyl Grignard Reagents." ChemInform 22, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199132117.

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21

Busacca, Carl A., Magnus C. Eriksson, and Rita Fiaschi. "ChemInform Abstract: Cross-Coupling of Vinyl Triflates and Alkyl Grignard Reagents Catalyzed by Nickel(0)-Complexes." ChemInform 30, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199928094.

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22

Iwasaki, Takanori, Yoshinori Miyata, Ryo Akimoto, Yuuki Fujii, Hitoshi Kuniyasu, and Nobuaki Kambe. "ChemInform Abstract: Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents." ChemInform 46, no. 5 (2015): no. http://dx.doi.org/10.1002/chin.201505055.

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23

BOGA, C., L. FORLANI, and P. E. TODESCO. "ChemInform Abstract: Unexpected Regioselectivity in the Attack of Vinyl Grignard Reagents to Bis(2-benzothiazolyl) Ketone." ChemInform 28, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199741094.

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24

NISHIYAMA, T., T. SESHITA, H. SHODAI, K. AOKI, H. KAMEYAMA, and K. KOMURA. "ChemInform Abstract: New Homocoupling Reaction of Alkyl, Aryl, Vinyl, and Allyl Grignard Reagents Using Trifluoromethanesulfonic Anhydride." ChemInform 27, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199648076.

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25

BARTOLI, G., M. BOSCO, R. DALPOZZO, G. PALMIERI, and E. MARCANTONI. "ChemInform Abstract: Reactivity of Nitro- and Nitrosoarenes with Vinyl Grignard Reagents: Synthesis of 2-(Trimethylsilyl)indoles." ChemInform 23, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199206172.

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26

Fujii, Yuuki, Jun Terao, Hiroyasu Watabe, Hiroyuki Watanabe, and Nobuaki Kambe. "Nickel-catalyzed dimerization coupling reactions of vinyl Grignard reagents with 3, 4-membered cyclic ethers and chlorosilanes." Tetrahedron 63, no. 28 (2007): 6635–41. http://dx.doi.org/10.1016/j.tet.2007.04.013.

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27

Gomtsyan, Arthur, Robert J. Koenig та Chih-Hung Lee. "ChemInform Abstract: Novel Sequential Process from N-Methoxyamides and Vinyl Grignard Reagents: New Synthesis of β-Aminoketones." ChemInform 32, № 38 (2010): no. http://dx.doi.org/10.1002/chin.200138086.

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28

Boga, Carla, Silvia Bordoni, Lucia Casarin, Gabriele Micheletti, and Magda Monari. "Regioselectivity in Reactions between Bis(2-benzothiazolyl)ketone and Vinyl Grignard Reagents: C- versus O-alkylation—Part III." Molecules 23, no. 1 (2018): 171. http://dx.doi.org/10.3390/molecules23010171.

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29

Douchez, Antoine, Azade Geranurimi та William D. Lubell. "Applications of γ,δ-Unsaturated Ketones Synthesized by Copper-Catalyzed Cascade Addition of Vinyl Grignard Reagents to Esters". Accounts of Chemical Research 51, № 10 (2018): 2574–88. http://dx.doi.org/10.1021/acs.accounts.8b00388.

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30

Smoliakova, Irina P., Ron Caple, Jay W. Brenny, et al. "Coupling of Grignard Reagents with ArSCl Adducts of Vinyl Ethers as a Useful Option for Formation of Carbon-Carbon Bonds." Synlett 1995, no. 03 (1995): 275–76. http://dx.doi.org/10.1055/s-1995-4934.

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31

Bartoli, Giuseppe, Gianni Palmieri, Marcella Bosco, and Renato Dalpozzo. "The reaction of vinyl grignard reagents with 2-substituted nitroarenes: A new approach to the synthesis of 7-substituted indoles." Tetrahedron Letters 30, no. 16 (1989): 2129–32. http://dx.doi.org/10.1016/s0040-4039(01)93730-x.

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32

SMOLIAKOVA, I. P., R. CAPLE, J. W. BRENNY, et al. "ChemInform Abstract: Coupling of Grignard Reagents with ArSCl Adducts of Vinyl Ethers as a Useful Option for Formation of Carbon-Carbon Bonds." ChemInform 26, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199532100.

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33

Singh, Om V., and Hyunsoo Han. "Stereoselective synthesis of trans-olefins by the copper-mediated SN2′ reaction of vinyl oxazines with Grignard reagents. Asymmetric synthesis of d-threo-sphingosines." Tetrahedron Letters 48, no. 13 (2007): 2345–48. http://dx.doi.org/10.1016/j.tetlet.2007.01.145.

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34

Organ, Michael G., and Aaron P. Murray. "Ni-Catalyzed Cross Coupling of Alkoxide-Containing Vinyl Halides with Grignard Reagents. A “One-Pot” Synthesis of 2-[(Trimethylsilyl)methyl]-2-propen-1-yl Acetate." Journal of Organic Chemistry 62, no. 5 (1997): 1523–26. http://dx.doi.org/10.1021/jo961900u.

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35

ORGAN, M. G., and A. P. MURRAY. "ChemInform Abstract: Ni-Catalyzed Cross Coupling of Alkoxide-Containing Vinyl Halides with Grignard Reagents. A “One-Pot” Synthesis of 2-((Trimethylsilyl)methyl)- 2-propen-1-yl Acetate." ChemInform 28, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199730065.

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36

Cai, Mingzhong, Jun Xia, and Pingping Wang. "A Facile Stereoselective Synthesis of (E)-1,2-disubstituted Vinyl Sulfides via Hydromagnesiation of Alkylarylacetylenes." Journal of Chemical Research 2005, no. 9 (2005): 583–84. http://dx.doi.org/10.3184/030823405774308989.

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Hydromagnesiation of alkylarylacetylenes 1 in diethyl ether gave (E)-α-arylvinyl Grignards reagents 2, which reacted with arylsulfenyl chlorides 3 to afford stereoselectively (E)-1,2-disubstituted vinyl sulfides 4 in good yields.

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37

Berg, Ulf, Nicolas Bodineau, Jean-Claude Négrel, et al. "Extension of the e.t. mechanism of aromatic nitration to the formation of Grignard reagents of RX (R = alkyl, aryl, cyclopropyl, vinyl). The ion pair collapse versus radical pair collapse hypothesis." Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry 4, no. 7 (2001): 567–70. http://dx.doi.org/10.1016/s1387-1609(01)01268-3.

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38

Chen, Yi, Wu, et al. "Synthesis of Silphenylene-Containing Siloxane Resins Exhibiting Strong Hydrophobicity and High Water Vapor Barriers." Coatings 9, no. 8 (2019): 481. http://dx.doi.org/10.3390/coatings9080481.

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The novel phenylenedisilane, 1,4-bis(dimethoxyphenylsilyl)benzene (BDMPD), was successfully synthesized via the reaction between trimethoxyphenylsilane (TMPS) and a Grignard reagent originating from 1,4-dibromobenzene. In comparison to common Grignard reactions, this process was a facile one-pot method. 1H NMR spectroscopy, FT-IR measurements, and elemental analysis confirmed the predicted structure of BDMPD. In addition, vinyl-terminated polysiloxanes containing silphenylene units (VPSSP), which were hydrolytically copolymerized from BDMPD, TMPS, and divinyltetramethyldisiloxane, exhibited ex

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39

Budarin, Vitaly L., James H. Clark, Sergey V. Mikhalovsky, Alina A. Gorlova, Nataly A. Boldyreva, and Vitaly K. Yatsimirsky. "The Hydrophobisation of Activated Carbon Surfaces by Organic Functional Groups." Adsorption Science & Technology 18, no. 1 (2000): 55–64. http://dx.doi.org/10.1260/0263617001493279.

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A technique of hydrophobic surface design with a high degree of structural homogeneity has been developed for catalytic materials. Mesoporous activated carbons and silica gel were modified by (A) treatment with vinyltrimethoxysilane (vtms) or (B) chlorination with carbon tetrachloride followed by reaction with a Grignard reagent. Evidence for silica gel modification was obtained from FT-IR and 13C NMR spectroscopy and from elemental analysis. Carbons chemically modified with alkanes and olefins were studied using thermogravimetry (TG) and the results compared with those for the modified silica

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40

Fujii, Yuuki, Jun Terao, Yuichiro Kato, and Nobuaki Kambe. "Titanocene-catalyzed alkylative dimerization of vinyl Grignard reagent using alkyl halides." Chemical Communications, no. 44 (2008): 5836. http://dx.doi.org/10.1039/b813596g.

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41

Tsai, Yeun-Min, та Jiuen-Ahn Sieh. "Organocopper Mediated Conjugate Addition of Vinyl Grignard Reagent toα,β-Unsaturated Acylsilane". Journal of the Chinese Chemical Society 46, № 5 (1999): 825–26. http://dx.doi.org/10.1002/jccs.199900111.

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42

Chelvam, Venkatesh, Ramesh Reddy, and Premansh Dudhe. "Synthesis of the Deacetoxytubuvaline Fragment of Pretubulysin and its Lipophilic Analogues for Enhanced Permeability in Cancer Cell Lines." Synlett 30, no. 01 (2018): 77–81. http://dx.doi.org/10.1055/s-0037-1611359.

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In the last two decades, tubulysins have emerged as alternatives to microtubule depolymerizing agents such as colchicine and vinblastine, which are well-established anticancer agents. However, the complex structure of tubulysins has always posed a challenge for synthetic chemists to scale up the production of these compounds. We report a new strategy for the practical gram-scale synthesis of a (4R)-4-[(tert-butoxycarbonyl)amino]-5-methylhexanoic acid through regioselective cleavage of a chiral aziridine ring with a vinyl Grignard reagent to afford tert-butyl [(1R)-1-isopropylbut-3-en-1-yl]carb

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43

Tanaka, Ryoichi, Hiroaki Sanjiki, and Hirokazu Urabe. "Yttrium-Mediated Conversion of Vinyl Grignard Reagent to a 1,2-Dimetalated Ethane and Its Synthetic Application." Journal of the American Chemical Society 130, no. 10 (2008): 2904–5. http://dx.doi.org/10.1021/ja077992u.

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44

Hansford, Karl A., James E. Dettwiler, and William D. Lubell. "One-Pot Synthesis of Homoallylic Ketones from the Addition of Vinyl Grignard Reagent to Carboxylic Esters." Organic Letters 5, no. 25 (2003): 4887–90. http://dx.doi.org/10.1021/ol0359822.

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45

Wang, Pei, Guo-Rong Ma, Sheng-Li Yu, and Chao-Shan Da. "Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs." Chirality 31, no. 1 (2018): 79–86. http://dx.doi.org/10.1002/chir.23038.

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46

Hansford, Karl A., Sergio Andres Perez Guarin, W. G. Skene, and William D. Lubell. "Bis(pyrrol-2-yl)arylenes from the Tandem Bidirectional Addition of Vinyl Grignard Reagent to Aryl Diesters." Journal of Organic Chemistry 70, no. 20 (2005): 7996–8000. http://dx.doi.org/10.1021/jo0510888.

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47

Nakamura, Eiichi, Katsumi Kubota, and Go Sakata. "Addition of Zincated Hydrazone to Vinyl Grignard Reagent. Ketone Synthesis by One-Pot Assembly of Four Components." Journal of the American Chemical Society 119, no. 23 (1997): 5457–58. http://dx.doi.org/10.1021/ja9706357.

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48

Watabe, Hiroyasu, Jun Terao, and Nobuaki Kambe. "Formation of 1,4-Disilyl-2-butenes from Vinyl Grignard Reagent and Chlorosilanes Catalyzed by a Titanocene Complex." Organic Letters 3, no. 11 (2001): 1733–35. http://dx.doi.org/10.1021/ol015928q.

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49

NAKAMURA, E., K. KUBOTA, and G. SAKATA. "ChemInform Abstract: Addition of Zincated Hydrazone to Vinyl Grignard Reagent. Ketone Synthesis by One-Pot Assembly of Four Components." ChemInform 28, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199739070.

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50

Boyce, Gregory R., and Jeffrey S. Johnson. "Three-Component Coupling Reactions of Silyl Glyoxylates, Vinyl Grignard Reagent, and Nitroalkenes: An Efficient, Highly Diastereoselective Approach to Nitrocyclopentanols." Angewandte Chemie International Edition 49, no. 47 (2010): 8930–33. http://dx.doi.org/10.1002/anie.201003470.

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