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Journal articles on the topic 'Grignard reactions'

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Published: 9 March 2023

Last updated: 10 March 2023

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1

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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2

Strickler, Rick R., John M. Motto, Craig C. Humber, and Adrian L. Schwan. "Stereospecific Grignard reactions of cholesteryl 1-alkenesulfinate esters: Application of the Andersen Protocol to the preparation of non-racemic α,β-unsaturated sulfoxides." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 423–30. http://dx.doi.org/10.1139/v03-002.

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Enantiomerically enriched α,β-unsaturated sulfinate esters of ()-cholesterol undergo stereospecific substitutions at sulfur when treated in benzene at 6°C with Grignard reagents. Sulfoxides with ees of 8599.5% are obtained when enantiopure sulfinates are used. The substitution reactions proceed with inversion of sulfur configuration. Enantiomerically pure cholesteryl (E)-2-carbomethoxyethenesulfinate is not a suitable reactant under the Grignard reaction conditions. It is suggested that the ester group induces unwanted reactions significantly lowering both the yield and sulfur stereogenicity.Key words: sulfinate, sulfoxide, Grignard reagents, stereospecific, unsaturated.

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3

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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4

Katritzky, Alan R., Stanislaw Rachwal, and Jing Wu. "A versatile method for the N, N-dialkylation of aromatic amines via Grignard reactions on N,N-bis(benzotriazolylmethyl)arylamines." Canadian Journal of Chemistry 68, no. 3 (March 1, 1990): 456–63. http://dx.doi.org/10.1139/v90-069.

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Grignard reactions of N,N-bis(benzotriazolylmethyl)arylamines afford the corresponding N,N-dialkylarylamines in high yields. Electron-releasing substituents on the aryl ring facilitate the reaction. Arylamines are N,N-dialkylated with two different alkyl groups by a stepwise procedure: N-benzotriazolylmethylation of an amine followed by a Grignard reaction to introduce the first alkyl group, and repetition of the same procedure to introduce the second alkyl group. Grignard reagents derived from 1,4-dihalobutane, upon reaction with N,N-bis(benzotriazolylmethyl)arylamines, give the corresponding N-aryl-hexahydroazepines together with acyclic products. Keywords: azepine, tertiary arylamines.

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5

Terao, Jun, Hirohisa Todo, Hiroyasu Watabe, Aki Ikumi, Yoshiaki Shinohara, and Nobuaki Kambe. "Carbon-carbon bond-forming reactions using alkyl fluorides." Pure and Applied Chemistry 80, no. 5 (January 1, 2008): 941–51. http://dx.doi.org/10.1351/pac200880050941.

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This account reviews C-C bond formation reactions using alkyl fluorides mostly focusing on the transition-metal-catalyzed reactions. These reactions proceed efficiently under mild conditions by the combined use of Grignard reagents and transition-metal catalysts, such as Ni, Cu, and Zr. It is proposed that ate complex intermediates formed by the reaction of these transition metals with Grignard reagents play important roles as the active catalytic species. Organoaluminun reagents react directly with alkyl fluorides in nonpolar solvents at room temperature to form C-C bonds. These studies demonstrate the practical usefulness of alkyl fluorides in C-C bond formation reactions and provide a promising method for the construction of carbon frameworks employing alkyl fluorides. The scope and limitations, as well as reaction pathways, are discussed.

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6

Clough, S., E. Goldman, S. Williams, and B. George. "Starting recalcitrant Grignard reactions." Journal of Chemical Education 63, no. 2 (February 1986): 176. http://dx.doi.org/10.1021/ed063p176.

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7

Li, Chao-Jun, Jianlin Huang, Xi-Jie Dai, Haining Wang, Ning Chen, Wei Wei, Huiying Zeng, et al. "An Old Dog with New Tricks: Enjoin Wolff–Kishner Reduction for Alcohol Deoxygenation and C–C Bond Formations." Synlett 30, no. 13 (June 13, 2019): 1508–24. http://dx.doi.org/10.1055/s-0037-1611853.

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The Wolff–Kishner reduction, discovered in the early 1910s, is a fundamental and effective tool to convert carbonyls into methylenes via deoxygenation under strongly basic conditions. For over a century, numerous valuable chemical products have been synthesized by this classical method. The reaction proceeds via the reversible formation of hydrazone followed by deprotonation with the strong base to give an N-anionic intermediate, which affords the deoxygenation product upon denitrogenation and protonation. By examining the mechanistic pathway of this century old classical carbonyl deoxygenation, we envisioned and subsequently developed two unprecedented new types of chemical transformations: a) alcohol deoxygenation and b) C–C bond formations with various electrophiles including Grignard-type reaction, conjugate addition, olefination, and diverse cross-coupling reactions.1 Introduction2 Background3 Alcohol Deoxygenation3.1 Ir-Catalyzed Alcohol Deoxygenation3.2 Ru-Catalyzed Alcohol Deoxygenation3.3 Mn-Catalyzed Alcohol Deoxygenation4 Grignard-Type Reactions4.1 Ru-Catalyzed Addition of Hydrazones with Aldehydes and Ketones4.2 Ru-Catalyzed Addition of Hydrazone with Imines4.3 Ru-Catalyzed Addition of Hydrazone with CO2 4.4 Fe-Catalyzed Addition of Hydrazones5 Conjugate Addition Reactions5.1 Ru-Catalyzed Conjugate Addition Reactions5.2 Fe-Catalyzed Conjugate Addition Reactions6 Cross-Coupling Reactions6.1 Ni-Catalyzed Negishi-type Coupling6.2 Pd-Catalyzed Tsuji–Trost Alkylation Reaction7 Other Reactions7.1 Olefination7.2 Heck-Type Reaction7.3 Ullmann-Type Reaction8 Conclusion and Outlook

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8

Yang, Yang, and Ji-Woong Lee. "Toward ideal carbon dioxide functionalization." Chemical Science 10, no. 14 (2019): 3905–26. http://dx.doi.org/10.1039/c8sc05539d.

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9

Shen, Lingyi, Yanxia Zhao, Dihua Dai, Ying-Wei Yang, Biao Wu, and Xiao-Juan Yang. "Stabilization of Grignard reagents by a pillar[5]arene host – Schlenk equilibria and Grignard reactions." Chemical Communications 56, no. 9 (2020): 1381–84. http://dx.doi.org/10.1039/c9cc08728a.

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10

Bell, KH, and LF Mccaffery. "Use of Menthyl 2-Methoxynaphthalene-1-sulfinates in the Andersen Synthesis of Optically Active Sulfoxides. Facile Cleavage by Grignard Reagents of Some Aromatic Methyl Ethers." Australian Journal of Chemistry 47, no. 10 (1994): 1925. http://dx.doi.org/10.1071/ch9941925.

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The pure crystalline diastereomers (1R,2S,5R)-menthyl (R)- and (S)-2-methoxynaphthalene-1-sulfinate (1b) have been prepared and, by reaction with Grignard reagents (the Andersen procedure), converted into optically active alkyl and aryl 2-methoxynaphthyl sulfoxides in 67-77% yields. Use of an excess of Grignard reagent results in facile O-alkyl cleavage of the methoxy group to the corresponding naphthol or a competing loss of the alkyl- or aryl- sulfinyl group to form 2-methoxynaphthalene. Pure diastereomers of menthyl 2,7- dimethoxynaphthalene-1-sulfinate (2b) and menthyl 4-methoxynaphthalene-1-sulfinate (3b) have also been prepared and their reactions with Grignard reagents have been studied.

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11

Smith, David H. "Grignard Reactions in "Wet" Ether." Journal of Chemical Education 76, no. 10 (October 1999): 1427. http://dx.doi.org/10.1021/ed076p1427.

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12

Delia, Thomas J. "Grignard Reactions Involving Halogenated Pyrimidines." Journal of Heterocyclic Chemistry 50, no. 4 (July 2013): 735–45. http://dx.doi.org/10.1002/jhet.1543.

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13

Desilva, AN, CL Francis, and AD Ward. "Grignard Addition Reactions to 1,4-Difunctionalized But-2-ynes." Australian Journal of Chemistry 46, no. 11 (1993): 1657. http://dx.doi.org/10.1071/ch9931657.

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Trisubstituted alkenes of E geometry have been prepared by anti addition of Grignard reagents to 1,4-difunctionalized but-2-ynes. Addition of primary, secondary and aromatic Grignard reagents to but-2-yne-1,4-diol provided (E)-2-substituted but-2-ene-1,4-diols as major products along with the corresponding 2-substituted buta-2,3-dien-1-ols. Addition of phenylmagnesium bromide to the mono- and di-methyl ethers of but-2-yne-1,4-diol gave 2,3-diphenyl-1,3-diene. Treatment of 4-dimethylaminobut-2-yn-1-ol with primary alkyl and alkenyl Grignard reagents afforded the 2-substituted anti addition product regiospecifically, stereospecifically and in high yield. Reaction of 1-dimethylamino-4-methoxybut-2-yne with butylmagnesium bromide provided only the 3-substituted anti addition product in good yield.

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14

Czaplik, Waldemar Maximilian, Matthias Mayer, Sabine Grupe, and Axel Jacobi von Wangelin. "On direct iron-catalyzed cross-coupling reactions." Pure and Applied Chemistry 82, no. 7 (May 2, 2010): 1545–53. http://dx.doi.org/10.1351/pac-con-09-10-10.

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A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.

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15

Shimizu, Makoto, Iwao Hachiya, Kazuki Ota, Shinya Fukumoto, Taiki Iwase, and Isao Mizota. "Umpolung Reactions of α-Tosyloximino Esters in a Flow System." Synlett 31, no. 19 (September 3, 2020): 1930–36. http://dx.doi.org/10.1055/s-0040-1707265.

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AbstractAn umpolung reaction of α-tosyloximino esters in a flow system is disclosed. Tandem N,N-dialkylations with two different Grignard reagents gave the desired N,N-dialkylated products in moderate to good yields. In addition, a tandem N,N,C-trialkylation of an α-tosyloximino ester with three different Grignard reagents has been successfully achieved to afford the desired N,N,C-trialkylated product in moderate yield.

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16

Bhat, Balkrishen, and A. P. Bhaduri. "Grignard Reaction of 2-Substituted-3-Cyanoquinolines." Zeitschrift für Naturforschung B 40, no. 7 (July 1, 1985): 990–95. http://dx.doi.org/10.1515/znb-1985-0724.

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Abstract Grignard reactions of 2-morpholino and 2-methylthio-3-cyanoquinoline, 2-chloro-3-cyanoquinoline, 2-chloro-3-cyano-6-methoxyquinoline and 2-chloro-3-cyano-7-methylquinoline with alkyl or aryl magnesium halides have been studied. It was found that 2-morpholino and 2-methylthio- 3-cyanoquinolines gave 1,4-addition products followed by rapid aromatisation. 2-Chloro-3- cyanoquinoline with alkyl magnesium halides furnished 1,4-addition products but with aryl magnesium halides 1,4- and 1,2-addition products were obtained. The cyano group of 4-aryl-2-chloro- 3-cyano-1,4-dihydroquinolines was found to participate in the Grignard reaction to yield 1,2- addition products. 2-Chloro-3-cyano-6-m ethoxyquinoline with alkyl and phenyl magnesium halides yielded exclusively 1,4-addition products. Similarly with p-m ethoxyphenyl magnesium bromide, 1,4-addition products were isolated which participated in the Grignard reaction to yield the expected adducts. Unlike the other chloroquinoline derivatives, 2-chloro-3-cyano-7-methylquinoline with alkyl magnesium halide formed 1 ,2-addition products but with aryl magnesium halides, 1,4-addition products were isolated. The 4-alkyl-2-chloro-3-cyano-l,4-dihydroquinolines were unstable as compared to their 4-aryl analogs. A couple of the Grignard reaction products were found to be unstable on activated surface.

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17

Weiss, Hilton M. "Side Reactions in a Grignard Synthesis." Journal of Chemical Education 76, no. 1 (January 1999): 76. http://dx.doi.org/10.1021/ed076p76.

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18

Brown, Bradley B., and Robert A. Volkmann. "Stereoselectivity in 6-halopenicillanate grignard reactions." Tetrahedron Letters 27, no. 14 (January 1986): 1545–48. http://dx.doi.org/10.1016/s0040-4039(00)84308-7.

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19

Handy, S. "Grignard Reactions in Imidazolium Ionic Liquids." Synfacts 2006, no. 8 (August 2006): 0827. http://dx.doi.org/10.1055/s-2006-942008.

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20

Williams, Lorenzo, Zhongda Zhang, Feng Shao, Patrick J. Carroll, and Madeleine M. Joullié. "Grignard reactions to chiral oxazolidine aldehydes." Tetrahedron 52, no. 36 (September 1996): 11673–94. http://dx.doi.org/10.1016/0040-4020(96)00672-2.

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21

Handy, Scott T. "Grignard Reactions in Imidazolium Ionic Liquids." Journal of Organic Chemistry 71, no. 12 (June 2006): 4659–62. http://dx.doi.org/10.1021/jo060536o.

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22

Semenov, V. V., E. Yu Ladilina, T. A. Chesnokova, N. K. Elistratova, Yu A. Kurskii, and N. P. Makarenko. "Reactions of methylchlorodisilanes with Grignard reagents." Russian Chemical Bulletin 44, no. 5 (May 1995): 927–30. http://dx.doi.org/10.1007/bf00696930.

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23

Kobayashi, Shoji, Keisuke Shibukawa, Yuta Miyaguchi, and Araki Masuyama. "Grignard Reactions in Cyclopentyl Methyl Ether." Asian Journal of Organic Chemistry 5, no. 5 (March 7, 2016): 636–45. http://dx.doi.org/10.1002/ajoc.201600059.

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24

URABE, H., and F. SATO. "ChemInform Abstract: Metal-Catalyzed (Grignard) Reactions." ChemInform 28, no. 4 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199704303.

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25

Salem, Mohammed A., Moustafa A. Gouda, and Ghada G. El-Bana. "Chemistry of 2-(Piperazin-1-yl) Quinoline-3-Carbaldehydes." Mini-Reviews in Organic Chemistry 19, no. 4 (June 2022): 480–95. http://dx.doi.org/10.2174/1570193x18666211001124510.

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Abstract: This review described the preparation of 2- chloroquinoline-3-carbaldehyde derivatives 18 through Vilsmeier-Haack formylation of N-arylacetamides and the use of them as a key intermediate for the preparation of 2-(piperazin-1-yl) quinoline-3-carbaldehydes. The synthesis of the 2- (piperazin-1-yl) quinolines derivatives was explained through the following chemical reactions: acylation, sulfonylation, Claisen-Schmidt condensation, 1, 3-dipolar cycloaddition, one-pot multicomponent reactions (MCRs), reductive amination, Grignard reaction and Kabachnik-Field’s reaction.

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26

Zeng, Xiaoming, and Xuefeng Cong. "Chromium-catalyzed transformations with Grignard reagents – new opportunities for cross-coupling reactions." Organic Chemistry Frontiers 2, no. 1 (2015): 69–72. http://dx.doi.org/10.1039/c4qo00272e.

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27

Novakov, I. A., B. S. Orlinson, E. N. Savel"ev, V. N. Urazbaev, and Yu B. Monakov. "Reactions of Grignard reagents with 1,3-dicyanoadamantane." Russian Chemical Bulletin 52, no. 9 (September 2003): 2048–51. http://dx.doi.org/10.1023/b:rucb.0000009650.93387.41.

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28

Brook, A. G., Pauline Chiu, John McClenaghnan, and Alan J. Lough. "Reactions of stable silenes with Grignard reagents." Organometallics 10, no. 9 (September 1991): 3292–301. http://dx.doi.org/10.1021/om00055a056.

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29

Tskhovrebov, Alexander G., Euro Solari, Rosario Scopelliti, and Kay Severin. "Reactions of Grignard Reagents with Nitrous Oxide." Organometallics 33, no. 10 (May 7, 2014): 2405–8. http://dx.doi.org/10.1021/om500333y.

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30

Maiorova, L. P., M. A. Katkova, T. V. Petrovskaya, S. Ya Khorshev, and M. N. Bochkarev. "Reactions of pentafluorophenylgermanium hydrides with Grignard reagents." Russian Chemical Bulletin 45, no. 1 (January 1996): 183–85. http://dx.doi.org/10.1007/bf01433759.

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31

Hessel, Günther, Günther Hulzer, Holger Kryk, and Wilfried Schmitt. "Investigation for Safer Initiation of Grignard Reactions." Chemie Ingenieur Technik 73, no. 6 (June 2001): 611. http://dx.doi.org/10.1002/1522-2640(200106)73:6<611::aid-cite6112222>3.0.co;2-7.

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32

Delia, Thomas J. "ChemInform Abstract: Grignard Reactions Involving Halogenated Pyrimidines." ChemInform 44, no. 42 (October 1, 2013): no. http://dx.doi.org/10.1002/chin.201342232.

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33

Jiao, Yinchun, Wenjing Zhao, Shuang Deng, Zilong Tang, Wanqiang Liu, Yichao Wan, and Fuqi Zhong. "A one-pot diastereoselective synthesis of 1,3-diols and 1,3,5-triols via cascade reactions of arylalkynyl Grignard reagents with enol esters." Journal of Chemical Research 44, no. 5-6 (March 4, 2020): 255–66. http://dx.doi.org/10.1177/1747519820908513.

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An efficient cascade reaction has been developed to synthesize a series of 1,3-diols and 1,3,5-triols via reactions of arylalkynyl Grignard reagents with enol esters. The stereoselectivity of reactions and the molecular configurations of the products were confirmed by nuclear magnetic resonance, X-ray diffraction, and high-performance liquid chromatography analysis. A possible reaction mechanism was analyzed with the results indicating that it proceeded through a 1,2-addition/rearrangement and reverse O-acylation to produce the 1,3-diol and via C-acylation to form the 1,3,5-triol.

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34

Bisz, Elwira. "Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates." Molecules 26, no. 19 (September 29, 2021): 5895. http://dx.doi.org/10.3390/molecules26195895.

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Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing β-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp2)–C(sp3) cross-coupling of aryl chlorides with Grignard reagents.

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35

Cooper, Alasdair K., Megan E. Greaves, William Donohoe, Paul M. Burton, Thomas O. Ronson, Alan R. Kennedy, and David J. Nelson. "Inhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles." Chemical Science 12, no. 42 (2021): 14074–82. http://dx.doi.org/10.1039/d1sc04582b.

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Nickel complexes with a dppf ligand can form inactive dinickel(ii) complexes during Suzuki–Miyaura cross-coupling reactions. However, these complexes can react with Grignard reagents in Kumada–Tamao–Corriu cross-coupling reactions.

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36

Berger, Anna Lucia, Karsten Donabauer, and Burkhard König. "Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions." Chemical Science 10, no. 48 (2019): 10991–96. http://dx.doi.org/10.1039/c9sc04987h.

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37

Jiang, Wen-Feng, Hui-Long Wang, and Zhe-Qi Li. "Improved synthesis of 6-(4-methoxyphenyl)-2,4-dichloro-1,3,5-triazine and 2,4-bis(resorcinyl)-substituted UV light absorbing derivatives." Journal of Chemical Research 2008, no. 11 (November 2008): 664–65. http://dx.doi.org/10.3184/030823408x375142.

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Pure 6-(4-methoxyphenyl)-2,4-dichloro-1,3,5-triazine was synthesised by a method that did not involve the troublesome Grignard reaction of 4-bromo-anisole. A series of bis(resorcinyl) triazine derivatives which can be used as UV light absorbers were subsequently prepared by utilising 6-(4-methoxyphenyl)-2,4-dichloro-1,3,5-triazine as the starting material via alkylation or acid-catalysed addition reactions.

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38

Konrad, David, Bilal Kicin, and Dirk Trauner. "Concise Asymmetric Synthesis of Kweichowenol A." Synlett 30, no. 04 (December 17, 2018): 383–86. http://dx.doi.org/10.1055/s-0037-1610390.

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An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.

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39

Cai, Ming-Zhong, Chun-Yun Peng, Hong Zhao, and Jia-Di Huang. "Stereoselective Synthesis of 1,3-enynylselenides via Palladium-Catalysed Cross Coupling Reactions." Journal of Chemical Research 2002, no. 8 (August 2002): 376–77. http://dx.doi.org/10.3184/030823402103172365.

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( E)-α-Bromovinylselenides undergo a cross coupling reaction with alkynyl Grignard reagents in the presence of tetrakis(triphenylphosphine)palladium(0) in THF at room temperature to afford 1,3-enynylselenides in good yields.

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40

Speight, Isaiah R., and Timothy P. Hanusa. "Exploration of Mechanochemical Activation in Solid-State Fluoro-Grignard Reactions." Molecules 25, no. 3 (January 28, 2020): 570. http://dx.doi.org/10.3390/molecules25030570.

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Owing to the strength of the C–F bond, the ‘direct’ preparation of Grignard reagents, i.e., the interaction of elemental magnesium with an organic halide, typically in an ethereal solvent, fails for bulk magnesium and organofluorine compounds. Previously described mechanochemical methods for preparing Grignard reagents have involved ball milling powdered magnesium with organochlorines or bromines. Activation of the C–F bond through a similar route is also possible, however. For example, milling 1- and 2-fluoronaphthalene with an excess of magnesium metal for 2 h, followed by treatment with FeCl3 and additional milling, produces the corresponding binaphthalenes, albeit in low yields (ca. 20%). The yields are independent of the particular isomer involved and are also comparable to the yields from corresponding the bromonaphthalenes. These results may reflect similar charges that reside on the α-carbon in the naphthalenes, as indicated by density functional theory calculations.

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41

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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42

Murai, Toshiaki, Yuuki Maekawa, Yuuki Hirai, Kazuma Kuwabara, and Mao Minoura. "Phosphonoselenoic acid esters from the reaction between phosphoroselenoyl chlorides and Grignard reagents: synthetic and stereochemical aspects." RSC Advances 6, no. 18 (2016): 15180–83. http://dx.doi.org/10.1039/c6ra00318d.

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KAWANA, Masajiro. "The reactions of sugar derivatives with grignard reagents." Journal of Synthetic Organic Chemistry, Japan 43, no. 3 (1985): 226–36. http://dx.doi.org/10.5059/yukigoseikyokaishi.43.226.

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Yamazaki, Takashi, Tsukasa Terajima, and Tomoko Kawasaki-Taskasuka. "Unusual reactions of Grignard reagents toward fluoroalkylated esters." Tetrahedron 64, no. 10 (March 2008): 2419–24. http://dx.doi.org/10.1016/j.tet.2008.01.015.

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Miles, William H., Sandra L. Rivera, and Jocelyn D. del Rosario. "Diastereoselective reactions of a simple secondary grignard reagent." Tetrahedron Letters 33, no. 3 (January 1992): 305–8. http://dx.doi.org/10.1016/s0040-4039(00)74117-7.

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Chen, Qing-Yun, Dong-Mei Shen, and Chao Liu. "Synthesis and Reactions of meso-Triphenylporphyrin Grignard Reagent." Synlett 2007, no. 19 (December 2007): 3068–72. http://dx.doi.org/10.1055/s-2007-992364.

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Orchin, Milton. "The Grignard reagent: Preparation, structure, and some reactions." Journal of Chemical Education 66, no. 7 (July 1989): 586. http://dx.doi.org/10.1021/ed066p586.

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Stockland, Robert A., Gordon K. Anderson, and Nigam P. Rath. "Reactions of [PdX2(dppm)] Complexes with Grignard Reagents." Organometallics 16, no. 23 (November 1997): 5096–101. http://dx.doi.org/10.1021/om970376u.

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Adrio, Javier, and Juan C. Carretero. "Functionalized Grignard Reagents in Kumada Cross-Coupling Reactions." ChemCatChem 2, no. 11 (August 16, 2010): 1384–86. http://dx.doi.org/10.1002/cctc.201000237.

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POLIVIN, YU N., M. E. PANINA, R. A. KARAKHANOV, and V. I. KELAREV. "ChemInform Abstract: Diethyl Ether Hydroperoxide in Grignard Reactions." ChemInform 25, no. 26 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199426088.

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