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Journal articles on the topic 'Reactif grignard'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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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

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

Wang, Xiang Cheng, Jian Li, Jian Bing, and Gao Yun Chen. "Study on Preparation of Octyltrimethoxysilane." Advanced Materials Research 712-715 (June 2013): 298–301. http://dx.doi.org/10.4028/www.scientific.net/amr.712-715.298.

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Octyltrimethoxysilane was synthesized by octane and trimethoxysilane, and octane was synthesized by grignard reagent. The main effects of reacting conditions on the yield were discussed and the optimum experimental conditions were studied. Used 3-bromopropene and 1-Brompentane as raw materials, the molar ratio of octane: magnesium was 1:1.2. Droplets time was 3 hours, the reacting time in 1 hour, and yield was 45.6%. Target compounds were analysised through GC-MS. Then, used choroplatinicacid isopropanol as catalyst, octane reacted with trimethoxysilane to gain octyltrimethoxysilane, the time of activation of catalyst was 1 hour ,reacting time 1 hour, and the yield was up to 65.4%. Study found that using 1-Brompentane Grignard reagent and 3-bromopropene could extend the carbon chain successfully. On the contrary, using 3-bromopropene Grignard reagent and 1-Brompentane to react, the rate of conversion was very low, a large number of decane generated, rather than octane.

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4

Grouiller, Annie, and Hassan Essadiq. "Behaviour of 2′-O-p-toluenesulfonyl uridine towards excess of a Grignard reagent." Canadian Journal of Chemistry 67, no. 4 (April 1, 1989): 708–9. http://dx.doi.org/10.1139/v89-108.

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Two C-methylated base nucleosides were obtained when 2′-O-tosyl-5′-O-trityluridine was reacted with 30 equivalents of methylmagnesium iodide. Keywords: nucleoside, Grignard reaction, C-methyl pyrimidinone, anhydro derivative, arabinofuranosyl.

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5

Chavan, Subhash P., Harshali S. Khatod, Tamal Das, and Kumar Vanka. "Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(−)-goniodiol." RSC Advances 6, no. 56 (2016): 50721–25. http://dx.doi.org/10.1039/c6ra03192g.

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6

Knochel, Paul, Eike Hupe, Wolfgang Dohle, David M. Lindsay, Véronique Bonnet, Guy Quéguiner, Andreas Boudier, et al. "Functionalized main-group organometallics for organic synthesis." Pure and Applied Chemistry 74, no. 1 (January 1, 2002): 11–17. http://dx.doi.org/10.1351/pac200274010011.

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Highly functionalized Grignard-reagents can be easily obtained by an iodinemagnesim exchange reaction and further reacted with various electrophiles. Via a BZn exchange reaction, a formal Michael addition with umpolung of the reactivity can be achieved. Chiral phosphine ligands can be easily synthesized by a 2.3 sigmatropic rearrangement and used successfully in asymmetric synthesis.

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7

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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8

Cai, Mingzhong, Chunyun Peng, Hong Zhao, and Wenyan Hao. "A Stereoselective Synthesis of (E)-Allylic Alcohols Via the Hydromagnesiation of Alkynylsilanes." Journal of Chemical Research 2003, no. 5 (May 2003): 296–98. http://dx.doi.org/10.3184/030823403103173877.

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Hydromagnesiation of alkynylsilanes 1 gives ( Z)-α-silylvinyl Grignard reagents 2, which are reacted with aldehydes or ketones to afford ( Z)-β-silyl allylic alcohols 3 in high yields; intermediates 3 can undergo the desilylation reaction in the presence of anhydrous KF to give ( E)-allylic alcohols 4 in good yields.

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9

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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10

Zhao, Hong, and Mingzhong Cai. "Alkynylsilanes as Convenient Precursors for the Stereoselective Synthesis of (E)-Disubstituted Alkenes." Journal of Chemical Research 2002, no. 12 (December 2002): 608–10. http://dx.doi.org/10.3184/030823402103170961.

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Hydromagnesiation of alkynylsilanes 1 gives (Z)-α-silylvinyl Grignard reagents 2, which are reacted with alkyl iodides or aryl iodides in the presence of CuI or Pd(PPh3)4 catalysts to afford (Z)-1,2-disubstituted vinylsilanes 3 in good yields. Intermediates 3 can undergo a desilylation reaction to give (E)-disubstituted alkenes 4 in high yields.

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11

Joshi, Rahul, Ritu Joshi, Changyeun Mo, Mohammad Akbar Faqeerzada, Hanim Z. Amanah, Rudiati Evi Masithoh, Moon S. Kim, and Byoung-Kwan Cho. "Raman Spectral Analysis for Quality Determination of Grignard Reagent." Applied Sciences 10, no. 10 (May 20, 2020): 3545. http://dx.doi.org/10.3390/app10103545.

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Grignard reagent is one of the most popular materials in chemical and pharmaceutical reaction processes, and requires high quality with minimal adulteration. In this study, Raman spectroscopic technique was investigated for the rapid determination of toluene content, which is one of the common adulterants in Grignard reagent. Raman spectroscopy is the most suitable spectroscopic method to mitigate moisture and CO2 interference in the molecules of Grignard reagent. Raman spectra for the mixtures of toluene and Grignard reagent with different concentrations were analyzed with a partial least square regression (PLSR) method. The combination of spectral wavebands in the prediction model was optimized with a variables selection method of variable importance in projection (VIP). The results obtained from the VIP-based PLSR model showed the reliable performance of Raman spectroscopy for predicting the toluene concentration present in Grignard reagent with a correlation coefficient value of 0.97 and a standard error of prediction (SEP) of 0.71%. The results showed that Raman spectroscopy combined with multivariate analysis could be an effective analytical tool for rapid determination of the quality of Grignard reagent.

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12

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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13

Lanza, Francesco, Juana Pérez, Ravindra Jumde, and Syuzanna Harutyunyan. "Lewis Acid Promoted Trapping of Chiral Aza-enolates." Synthesis 51, no. 05 (January 29, 2019): 1253–62. http://dx.doi.org/10.1055/s-0037-1611657.

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We present a study on sequential conjugate addition of Grignard reagents to alkenyl-heteroarenes followed by trapping of the resulting enolates, yielding moderate to good diastereoselectivities. Contrary to conventional wisdom, one-pot conjugate addition/trapping using two reactive Michael acceptors in combination with Grignard reagents can proceed via conjugate addition to the least reactive Michael acceptor. This unusual chemoselectivity is triggered by the presence of a Lewis acid, reverting the usual reactivity order of Michael acceptors.

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14

Seto, Chika, Takeshi Otsuka, Yoshiki Takeuchi, Daichi Tabuchi, and Takashi Nagano. "Iron-Catalyzed Grignard Cross-Couplings with Allylic Methyl Ethers or Allylic Trimethylsilyl Ethers." Synlett 29, no. 09 (March 19, 2018): 1211–14. http://dx.doi.org/10.1055/s-0036-1591774.

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We have found that cross-coupling between aryl Grignard reagents and allylic methyl ethers proceeded well in the presence of a catalytic amounts of Fe(acac)3 to afford the corresponding allylic substitution products in good yields. Under the same conditions, allylic trimethylsilyl ethers also reacted with Grignard reagents to give the corresponding cross-coupling products.

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15

Usami, Shun, Tomoyuki Suzuki, Koudai Mano, Kosaku Tanaka, Yoshimitsu Hashimoto, Nobuyoshi Morita, and Osamu Tamura. "Chelation-Based Homologation by Reaction of Organometallic Reagents with O-Alkyl S-Pyridin-2-yl Thiocarbonates: Synthesis of Esters from Grignard Reagents." Synlett 30, no. 13 (June 27, 2019): 1561–64. http://dx.doi.org/10.1055/s-0037-1611868.

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The one-carbon homologative esterification of Grignard reagents with O-alkyl S-pyridin-2-yl thiocarbonates has been explored. This one-step synthesis of esters from Grignard reagents is the first case to involve chelation-stabilized intermediates.

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16

Kubo, Hajime, Shigeru Ohmiya, and Isamu Murakoshi. "Absolute stereochemistry of (−)-camoensine and (−)-camoensidine in Maackia species." Canadian Journal of Chemistry 72, no. 1 (January 1, 1994): 214–17. http://dx.doi.org/10.1139/v94-033.

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It was demonstrated that the attack of Grignard reagents such as methyl-, allyl-, and 3,3-dimethoxypropyl magnesium bromides on 11,12-dehydrocytisine occurs on the α-face, to give the corresponding 11α-alkylcytisine. (−)-Camoensine and (−)-camoensidine were synthesized from (−)-cytisine via the Grignard reaction. The absolute stereochemistry of the above alkaloids was confirmed to be 7R, 9R, 11R and 6S, 7R, 9R, 11R, respectively.

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17

El-Aal, Abd, and Ali Khalaf. "Modern Friedel-Crafts chemistry: Part 36. Facile synthesis of some new pyrido[3,2,1-jk]carbazoles via Friedel-Crafts cyclialkylations." Journal of the Serbian Chemical Society 78, no. 5 (2013): 611–19. http://dx.doi.org/10.2298/jsc120520098a.

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An efficient methodology for the synthesis of novel substituted pyrido[3,2,1-jk]carbazole via Friedel-Crafts cyclialkylations is reported. The methodology was realized by three-step protocol involved the addition of carbazole to 3-methylcrotononitrile. The resulted nitrile was hydrolyzed to desired ester, followed by addition of Grignard reagents to afford tertiary alcohols and/or reacted directly with different Grignard reagent to form the desired ketones. The later ketones were converted to both secondary and tertiary alcohols by reduction with LAH and addition of Grignard reagents respectively. These carbinols were cyclialkylated under Friedel-Crafts conditions catalyzed by AlCl3/CH3NO2, PTSA and PPA to give tri-and tetrasubstituted pyrido[3,2,1-jk]carbazole.

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18

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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19

Stachel, Hans-Dietrich, and Josef Schachtner. "Synthese von Heteroanaloga der Penicillsäure / Synthesis of Hetero Analogues of Penicillic Acid." Zeitschrift für Naturforschung B 51, no. 9 (September 1, 1996): 1334–38. http://dx.doi.org/10.1515/znb-1996-0919.

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20

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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21

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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22

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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23

Narasaka, Koichi. "Metal-assisted amination with oxime derivatives." Pure and Applied Chemistry 74, no. 1 (January 1, 2002): 143–49. http://dx.doi.org/10.1351/pac200274010143.

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Electrophilic amination of Grignard reagents is accomplished by using O-sulfonyl-oximes of benzophenone derivatives. In the presence of a catalytic amount of CuCN, O-sulfonyloxime of 4,4¢-bis(trifluoromethyl)benzophenone reacts with alkyl Grignard reagents in tetrahydrofuran (THF) and hexamethylphosphoramide (HMPA), yielding primary alkyl-amines by successive hydrolysis of the resulting N-alkylimines. Arylamines are also prepared as well as alkylamines by treating O-sulfonyloxime of 3,3¢,5,5¢-tetrakis(trifluoromethyl)benzophenone in toluene-ether with Grignard reagents. Various cyclic imines are synthesized by palladium-catalyzed cyclization of olefinic oxime derivatives. That is, the reaction of O-pentafluorobenzoyloximes of olefinic ketones with a catalytic amount of Pd(PPh3)4 and triethylamine in dimethylformamide (DMF) affords nitrogen-containing heterocycles, such as pyrroles, pyridines, isoquinolines, spiro-imines, and aza-azulenes. This reaction proceeds via the initial formation of alkylideneaminopalladium species generated by oxidative addition of oximes to Pd(0), and the successive intramolecular Heck-type amination occurs on the olefinic moiety.

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24

Williamson, Kenneth L. "Starting the Grignard reaction." Journal of Chemical Education 65, no. 4 (April 1988): 376. http://dx.doi.org/10.1021/ed065p376.1.

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25

Shimizu, Makoto, Yuki Furukawa, Isao Mizota, and Yusong Zhu. "An umpolung reaction of α-iminonitriles and its application to the synthesis of aminomalononitriles." New Journal of Chemistry 44, no. 1 (2020): 152–61. http://dx.doi.org/10.1039/c9nj05114g.

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26

Silva, Pedro J., and Carlos E. P. Bernardo. "Unveiling the Reaction Mechanism of the Das/Chechik/Marek Synthesis of Stereodefined Quaternary Carbon Centers." Applied Sciences 11, no. 11 (May 28, 2021): 5002. http://dx.doi.org/10.3390/app11115002.

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The reaction mechanism of the Cu+-catalyzed introduction of two all-carbon-substituted stereocenters in an ynamide system using a Grignard reagent, a zinc carbenoid, and an aldehyde, was investigated using density-functional theory. In contrast to the formation of an organocopper(I) compound and subsequent carbocupration reaction, previously postulated as the initial step, the reaction proved to instead proceed through an initial complexation of the substrate alkyne bond by the Cu+-catalyst, which primes this bond for reaction with the Grignard reagent. Subsequent addition of the zinc carbenoid then enables the nucleophilic attack on the incoming aldehyde, which is revealed as the rate-limiting step. Our computations have also identified the factors governing the regio- and setereoselectivity of this interesting reaction, and suggest possible paths for its further development.

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27

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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28

Xie, Lan-Gui, and Darren J. Dixon. "Tertiary amine synthesis via reductive coupling of amides with Grignard reagents." Chem. Sci. 8, no. 11 (2017): 7492–97. http://dx.doi.org/10.1039/c7sc03613b.

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29

Wang, Jiajia, Yijie Luo, Kaikai Jin, Chao Yuan, Jing Sun, Fengkai He, and Qiang Fang. "A novel one-pot synthesized organosiloxane: synthesis and conversion to directly thermo-crosslinked polysiloxanes with low dielectric constants and excellent thermostability." Polymer Chemistry 6, no. 33 (2015): 5984–88. http://dx.doi.org/10.1039/c5py00823a.

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30

Hossain, Md Zakir, and Maisarah B. A. Razak. "Halogenation of epitaxial graphene grown on the Si-face of the SiC(0001) substrate and its further reaction with Grignard reagent." New Journal of Chemistry 40, no. 2 (2016): 1671–78. http://dx.doi.org/10.1039/c5nj02642c.

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31

Paryzek, Zdzislaw, and Krzysztof Blaszczyk. "Spiro steroids via the Barbier–Grignard reaction of steroidal ketones with allyl bromide and magnesium." Canadian Journal of Chemistry 65, no. 1 (January 1, 1987): 229–33. http://dx.doi.org/10.1139/v87-037.

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Barbier–Grignard reaction of 3- and 17-steroidal ketones gave excellent yields of the allyl steroids 1 + 2 and 15. These were transformed into a mixture of 1,3- and 1,4-diols by hydroboration–oxidation. The diols 3,5, and 18 were used for the preparation of spirolactones and spiroethers. Thus, the Barbier–Grignard allylation–hydroboration–cyclization sequence proved to be an effective method for the spiroannelation of steroidal ketones. It was also shown that an earlier assignment of the stereochemistry of the diols 3 and 5 was erroneous.

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32

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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33

Hatamzadeh, Maryam, and Mehdi Jaymand. "Synthesis and characterization of polystyrene-graft-polythiophene via a combination of atom transfer radical polymerization and Grignard reaction." RSC Adv. 4, no. 32 (2014): 16792–802. http://dx.doi.org/10.1039/c4ra01228c.

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34

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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35

Ikuma, Naohiko, Koji Nakagawa, Ken Kokubo, and Takumi Oshima. "Regioselective addition of Grignard reagents to tosylazafulleroid and derivatization to 1,2-disubstituted [60]fullerene." Organic & Biomolecular Chemistry 14, no. 29 (2016): 7103–8. http://dx.doi.org/10.1039/c6ob00869k.

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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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37

Vetter, Anna C., Kirill Nikitin, and Declan G. Gilheany. "Long sought synthesis of quaternary phosphonium salts from phosphine oxides: inverse reactivity approach." Chemical Communications 54, no. 46 (2018): 5843–46. http://dx.doi.org/10.1039/c8cc02173b.

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Setiawati, Evy, and Khoerul Anwar. "SINTESIS FEROMON 3-METIL 4-OKTANOL SEBAGAI ZAT PEMBASMI HAMA KUMBANG KELAPA Rhynchoporus spp." Jurnal Riset Industri Hasil Hutan 3, no. 2 (December 31, 2011): 27. http://dx.doi.org/10.24111/jrihh.v3i2.1191.

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The compound of 3-methyl-4-octanol had been synthesized by the formation of Grignard reagent sec-buthyl magnesium bromide. The choosing of reactant 2-bromo butane and n-pentanal were resulted from retrosynthesize analysize of 3-methyl-4octanol pheromone. The reaction of sec-buthyl magnesium bromide was done at temperature 400C for 30 minutes, while the reaction between this reagent with n-pentanal was done for two hours. The formed compound was hydrolized using saturated NH4Cl solution and then cooled. The compound was identified using Infra Red spectrophotometre (IR), Gas Chromatography (GC), and Gas Chromatography-Mass Spectroscopy (GC-MS). The yield persentage of the compound was 12,70%.Keywords: synthesis, hydrolisis, pheromone, Grignard reagent, Rhynchoporus spp

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Lee, Boeun, Jae-Hyun Cho, Hyo Ree Seo, Su Bin Na, Jong Hak Kim, Byung Won Cho, Taeeun Yim, and Si Hyoung Oh. "Strategic combination of Grignard reagents and allyl-functionalized ionic liquids as an advanced electrolyte for rechargeable magnesium batteries." Journal of Materials Chemistry A 6, no. 7 (2018): 3126–33. http://dx.doi.org/10.1039/c7ta09330f.

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40

Li, Jialun, Michinari Seki, Shintaro Kamio, and Hiroto Yoshida. "Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H–B(dan) as a B(dan) electrophile." Chemical Communications 56, no. 47 (2020): 6388–91. http://dx.doi.org/10.1039/d0cc02560g.

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41

Lee, Jae Wook, Jacqueline T. Bork, Hyung-Ho Ha, Animesh Samanta, and Young-Tae Chang. "Novel Orthogonal Synthesis of a Tagged Combinatorial Triazine Library via Grignard Reaction." Australian Journal of Chemistry 62, no. 9 (2009): 1000. http://dx.doi.org/10.1071/ch09153.

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To expand the diversity of 1,3,5-triazine libraries to aryl and alkyl functionalities through the C–C bond, we employed a novel orthogonal synthesis via Grignard monoalkylation or monoarylation of cyanuric chloride in solution to prepare aryl- or alkyl-substituted triazine building blocks. These aryl- or alkyl-substituted triazine building blocks were captured by a resin-bound amine, followed by amination and acidic cleavage with high purity. Herein, we demonstrate a novel orthogonal synthesis of a tagged aryl- and alkyl-triazine library on solid support, utilizing building blocks prepared via Grignard reaction in solution. Through incorporation of a triethylene glycol linker at one of the alternate sites on the triazine scaffold we explored an intrinsic tagged library approach.

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42

Binyamin, Iris, Shoval Meidan-Shani, and Nissan Ashkenazi. "Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors." Beilstein Journal of Organic Chemistry 11 (July 30, 2015): 1332–39. http://dx.doi.org/10.3762/bjoc.11.143.

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The synthesis of P-chirogenic (±)-phosphine oxides and phosphinates via selective nucleophilic ring opening of the corresponding oxaphospholanes is described. Two representative substrates: the phosphonate 2-ethoxy-1,2-oxaphospholane 2-oxide and the phosphinate 2-phenyl-1,2-oxaphospholane 2-oxide were reacted with various Grignard reagents to produce a single alkyl/aryl product. These products may possess further functionalities in addition to the phosphorus center such as the γ-hydroxypropyl group which results from the ring opening and π-donor moieties such as aryl, allyl, propargyl and allene which originates from the Grignard reagent.

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Wang, Yang, Qiang Li, Xian Feng Gong, Xue Ling Zhao, and Yu Zhang. "Study on Synthesis of 2-Hydroxy-6-Naphthoic Acid from 2-Naphthol and Improve the Synthetic Process." Advanced Materials Research 634-638 (January 2013): 2044–48. http://dx.doi.org/10.4028/www.scientific.net/amr.634-638.2044.

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2-Hydroxy-6-naphthoic acid is an main raw material for the synthesis of polyaromatic ester, it was synthesized from 2-Naphthol by methoxylation, bromization, grignard reaction and demethylation before recrystallization (C2H5OH:H2O=2.8:1 m/m) with an overall yield of 78.5% and content of 99.1%. Furthermore, the results showed that the 6-bromo-2-methoxynaphthalene was prepared using Sn as reducing agent with 96.2% of the yield which is higher than 6-bromo-2-methoxynaphthalene was prepared using solid carbon dioxide and grignard reagent with 23.8% of the yield.

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Hossain, M. Z., H. Yoko, and M. A. M. Jusoh. "Organic functionalization of epitaxial graphene on SiC through direct binding of transient radicals from the reaction mixture." Chemical Communications 52, no. 100 (2016): 14380–83. http://dx.doi.org/10.1039/c6cc08632b.

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Cai, Mingzhong, Wenyan Hao, Hong Zhao, and Caisheng Song. "Stereoselective Synthesis of 1,3-Enynylsilanes via Hydromagnesiation Reaction of Alkynylsilanes." Journal of Chemical Research 2003, no. 8 (August 2003): 485–86. http://dx.doi.org/10.3184/030823403103174623.

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Hydromagnesiation of alkynylsilanes gives ( Z)-α-silylvinyl Grignard reagents, which are cross-coupled with alkynyl iodides in the presence of tetrakis(triphenylphosphine)palladium(0) catalyst to afford stereoselectively 1,3-enynylsilanes in good yields.

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Strunz, George M., Richard Bethell, Glen Sampson, and Peter White. "On the Baylis–Hillman reaction of acrylate, acrylonitrile, and acrolein with some non-enolizable α-dicarbonyl compounds: synthesis of phytotoxic bipolaroxin models." Canadian Journal of Chemistry 73, no. 10 (October 1, 1995): 1666–74. http://dx.doi.org/10.1139/v95-206.

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The Baylis–Hillman reaction of acrylonitrile, methyl acrylate, and acrolein with several cyclic α-dicarbonyl compounds was investigated. Whereas acrylonitrile reacted with most of these ketones, giving good yields of the expected 1′-cyanovinyl carbinols, the more sterically demanding methyl acrylate failed to undergo the reaction. Attempted Baylis–Hillman reaction of acrolein with the 1,2-dicarbonyl substrates usually resulted in polymers but, in two cases, the desired α-substituted acroleins were obtained. An alternative route to such compounds was developed, employing a Grignard – allylic oxidation sequence. In bioassays, some of the products, embodying the functionality believed responsible for the phytotoxicity of the sesquiterpene bipolaroxin, inhibited germination of lettuce seeds. This activity diminished with time. Keywords: Baylis–Hillman, acrylonitrile, acrylate, acrolein, α-dicarbonyl, bipolaroxin, phytotoxicity.

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Harkness, Gavin J., and Matthew L. Clarke. "Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers." Catalysis Science & Technology 8, no. 1 (2018): 328–34. http://dx.doi.org/10.1039/c7cy01205e.

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The challenging reaction of unactivated ortho-substituted aromatic ethers with Grignard reagents has been found to be most effectively catalysed using nickel complexes of less sterically hindered ligands.

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48

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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49

Bella, Maroš, Bohumil Steiner, Vratislav Langer, and Miroslav Koóš. "Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus o-tolyl rearrangement." Beilstein Journal of Organic Chemistry 10 (August 20, 2014): 1942–50. http://dx.doi.org/10.3762/bjoc.10.202.

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The Grignard reaction of 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside and benzylmagnesium chloride (or bromide) afforded a non-separable mixture of diastereomeric benzyl carbinols and diastereomeric o-tolyl carbinols. The latter resulted from an unexpected benzyl to o-tolyl rearrangement. The proportion of benzyl versus o-tolyl derivatives depended on the reaction conditions. Benzylmagnesium chloride afforded predominantly o-tolyl carbinols while the application of benzylmagnesium bromide led preferably to the o-tolyl carbinols only when used in excess or at higher temperatures. The structures of the benzyl and o-tolyl derivatives were confirmed unambiguously by NMR spectral data and X-ray crystallographic analysis of their 5-ketone analogues obtained by oxidation of the corresponding mixture of diastereomeric carbinols. A possible mechanism for the Grignard reaction leading to the benzyl→o-tolyl rearrangement is also proposed.

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50

Szczerbowski, Daiane, Stefan Schulz, and Paulo Henrique Gorgatti Zarbin. "Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug Edessa meditabunda." Organic & Biomolecular Chemistry 18, no. 26 (2020): 5034–44. http://dx.doi.org/10.1039/d0ob00862a.

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A convergent synthetic route was developed for the stereoselective synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate. The Fouquet-Schlosser variant of the Grignard reaction was used as key steps.

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