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Journal articles on the topic 'Grignard reagents'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 March 2023

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1

Narayanaperumal, Senthil, Ricardo S. Schwab, Wystan K. O. Teixeira, and Danilo Yano de Albuquerque. "Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds." Synthesis 52, no. 13 (March 16, 2020): 1855–73. http://dx.doi.org/10.1055/s-0039-1690847.

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Enantiomerically enriched diaryl, aryl heteroaryl, and diheteroaryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

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2

Fujdala, Kyle L., David W. K. Gracey, Erica F. Wong, and Kim M. Baines. "The addition of organometallic reagents to tetramesityldigermene." Canadian Journal of Chemistry 80, no. 11 (November 1, 2002): 1387–92. http://dx.doi.org/10.1139/v02-128.

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The thermolysis and photolysis of hexamesitylcyclotrigermane in the presence of ethylmagnesium bromide has been investigated. Under photochemical conditions, ethyldimesitylgermane, 1,2-diethyl-1,1,2-trimesityldigermane and ethyl-1,1,2,2-tetramesityldigermane were isolated and, under thermal conditions, 1,2,2-triethyl-1,1-dimesityl digermane and 2,2-diethyl-1,1,1-trimesityldigermane were isolated. The photolysis of hexamesitylcyclotrigermane in the presence of methyllithium has also been investigated. In both cases, the organometallic reagent adds to tetramesityl digermene and dimesitylgermylene formed by photochemical or thermal cleavage of the cyclotrigermane. In the case of the addition of the Grignard reagent, the resulting germyl Grignard reagent undergoes a facile ligand exchange reaction.Key words: digermene, germylene, Grignard reagents, alkyllithium reagents, germylmagnesium compounds, germyllithium compounds.

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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

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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5

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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6

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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7

Caillé, Julien, Fatma Boukattaya, Fabien Boeda, Morwenna S. M. Pearson-Long, Houcine Ammar, and Philippe Bertus. "Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives." Organic & Biomolecular Chemistry 16, no. 9 (2018): 1519–26. http://dx.doi.org/10.1039/c7ob03047a.

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8

Seyferth, Dietmar. "The Grignard Reagents." Organometallics 28, no. 6 (March 23, 2009): 1598–605. http://dx.doi.org/10.1021/om900088z.

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9

Tjurina, Ljudmila A., Vladimir V. Smirnov, Gennadii B. Barkovskii, Eugenii N. Nikolaev, Stanislav E. Esipov, and Irina P. Beletskaya. "Cluster Grignard Reagents." Organometallics 20, no. 12 (June 2001): 2449–50. http://dx.doi.org/10.1021/om0100380.

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10

Gilman, Henry, and A. P. Hewlett. "Furan grignard reagents." Recueil des Travaux Chimiques des Pays-Bas 51, no. 1 (September 3, 2010): 93–97. http://dx.doi.org/10.1002/recl.19320510107.

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11

Wang, Wei, Jiancun Gao, Chenguang Shi, Shengnan Wang, Yujing Li, Xiong Dai, and Tianmeng Jiang. "Thermal Hazards of Synthesizing a Grignard Reagent under Different Dosing Rates." International Journal of Chemical Engineering 2022 (March 26, 2022): 1–10. http://dx.doi.org/10.1155/2022/6776179.

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Thermal safety during the synthesis of a Grignard reagent under different dosing rates was evaluated in this work. A reaction calorimeter (SIMULAR) was used to investigate the heat release under isothermal experiment in the range of 0.5–2.0 g⋅min−1 dosing rates. The thermal decomposition of the Grignard reagent was analyzed using accelerating rate calorimetry (ARC). Furthermore, the risk assessment of thermal runaway was analyzed using a risk matrix and a Stoessel criticality diagram. The results indicate that decreasing the dosing rate can decrease the risk level of synthesizing the Grignard reagent from class 3 to class 1. However, the risk level was class 3 at different dosing rates when the induction period was considered. In the case of cooling failure, the most hazardous moment was the induction period, followed by the dosing period. These findings provide further evidence that the dose rate of 0.5 g⋅min−1 was safer to produce Grignard reagents.

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12

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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13

Pace, Vittorio, Serena Monticelli, Karen de la Vega-Hernández, and Laura Castoldi. "Isocyanates and isothiocyanates as versatile platforms for accessing (thio)amide-type compounds." Organic & Biomolecular Chemistry 14, no. 33 (2016): 7848–54. http://dx.doi.org/10.1039/c6ob00766j.

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The addition of carbon (Grignard and organolithium reagents) and hydride nucleophiles (Schwartz reagent) to isocyanates and isothiocyanates constitutes a versatile, direct and high yielding approach to the synthesis of functionalized (thio)amide derivatives including haloamides and formamides.

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14

Hölzer, Bettina, and Reinhard W. Hoffmann. "Kumada–Corriu coupling of Grignard reagents, probed with a chiral Grignard reagent." Chemical Communications, no. 6 (February 19, 2003): 732–33. http://dx.doi.org/10.1039/b300033h.

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15

Bellinger, Tania J., Teavian Harvin, Ti’Bran Pickens-Flynn, Nataleigh Austin, Samuel H. Whitaker, Mai Ling C. Tang Yuk Tutein, Dabria T. Hukins, Nichele Deese, and Fenghai Guo. "Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone." Molecules 25, no. 9 (May 1, 2020): 2128. http://dx.doi.org/10.3390/molecules25092128.

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Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN∙2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.

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16

Berton, Mateo, Kevin Sheehan, Andrea Adamo, and D. Tyler McQuade. "Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides." Beilstein Journal of Organic Chemistry 16 (June 19, 2020): 1343–56. http://dx.doi.org/10.3762/bjoc.16.115.

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Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.

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17

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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18

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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19

Li, Feng, Zhao-Ming Li, Hua Yang, and Volker Jäger. "New Approaches to Branched β-Amino α-Hydroxy Acids, Taxol Side-chain Analogs." Zeitschrift für Naturforschung B 63, no. 4 (April 1, 2008): 431–46. http://dx.doi.org/10.1515/znb-2008-0410.

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AbstractThe phenylisothreonine derivatives, taxol side-chain analogs, were synthesized by two routes, one based on the highly stereoselective addition of a phenyl Grignard reagent to the L-threose-derived nitrone 7, and the other using asymmetric α-alkoxyallylation of the ketimine 20 with chiral allyl boron reagents.

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20

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 (November 1, 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 followed by Paal–Knorr condensation with ammonium formate.Key words: copper-catalyzed cascade addition, homoallylic ketone, alkyl-substituted vinyl Grignard reagents, ozonolysis, pyrrole, γ,δ-unsaturated ketone.

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21

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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22

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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23

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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24

Kale, Mohan B., Shrikant B. Jagtap, and Santosh S. Devkate. "CuSCN Catalyzed Conjugate Addition of Grignard Reagents to Substituted Coumarins with Dilithium Tetrachloromanganate." Asian Journal of Chemistry 32, no. 7 (2020): 1793–98. http://dx.doi.org/10.14233/ajchem.2020.22701.

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The regioselective 1,4-addition of CuSCN catalyzed Grignard reagents to the substituted coumarins are reported. The Li2MnCl4 reagent is used to transmetallate magnesium by manganese. It adds regioselectively to coumarins and forms 1,4-addition products with higher yield under the atmosphere of nitrogen gas and at a lower temperature

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25

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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26

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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27

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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28

Ingraham, Lloyd L. "B12 COENZYMES: BIOLOGICAL GRIGNARD REAGENTS." Annals of the New York Academy of Sciences 112, no. 2 (December 16, 2006): 713–20. http://dx.doi.org/10.1111/j.1749-6632.1964.tb45049.x.

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29

Law, Man Chun, Kwok-Yin Wong, and Tak Hang Chan. "Grignard reagents in ionic liquids." Chemical Communications, no. 23 (2006): 2457. http://dx.doi.org/10.1039/b602718k.

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30

Vestergren, Marcus, Johan Eriksson, and Mikael Håkansson. "Chiral cis-octahedral Grignard reagents." Journal of Organometallic Chemistry 681, no. 1-2 (September 2003): 215–24. http://dx.doi.org/10.1016/s0022-328x(03)00616-8.

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31

Bickelhaupt, F. "Di-Grignard reagents and metallacycles." Pure and Applied Chemistry 58, no. 4 (January 1, 1986): 537–42. http://dx.doi.org/10.1351/pac198658040537.

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32

Sassian, M., D. Panov, and A. Tuulmets. "Grignard reagents in toluene solutions." Applied Organometallic Chemistry 16, no. 9 (2002): 525–29. http://dx.doi.org/10.1002/aoc.333.

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33

Holloway, Clive E., and Milan Melnik. "Structural aspects of grignard reagents." Coordination Chemistry Reviews 135-136 (November 1994): 287–301. http://dx.doi.org/10.1016/0010-8545(94)80070-7.

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34

Schulz, Thomas, and Dietmar Stalke. "Magnesium Triimidosulfonates from Grignard Reagents." European Journal of Inorganic Chemistry 2010, no. 14 (April 7, 2010): 2185–92. http://dx.doi.org/10.1002/ejic.201000046.

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35

Goodwin, Conrad A. P., Alex Smith, Fabrizio Ortu, Iñigo J. Vitorica-Yrezabal, and David P. Mills. "Salt metathesis versus protonolysis routes for the synthesis of silylamide Hauser base (R2NMgX; X = halogen) and amido-Grignard (R2NMgR) complexes." Dalton Transactions 45, no. 14 (2016): 6004–14. http://dx.doi.org/10.1039/c5dt02535d.

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The effectiveness of simple synthetic routes to access silylamide Hauser base (R₂NMgX; X = halogen) and amido-Grignard (R₂NMgR) complexes from commercially available Grignard reagents is explored herein.

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36

García-Viñuales, Sara, Ignacio Delso, Pedro Merino, and Tomás Tejero. "Stereoselective Ethynylation and Propargylation of Chiral Cyclic Nitrones: Application to the Synthesis of Glycomimetics." Synthesis 48, no. 19 (July 11, 2016): 3339–51. http://dx.doi.org/10.1055/s-0035-1562500.

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Ethynylation and propargylation of chiral nonracemic polyhydroxylated cyclic nitrones with Grignard reagents are efficient methods for preparing building blocks containing an alkyne moiety to be used in copper-catalyzed azide alkyne cycloaddition click chemistry. Whereas ethynylation takes place with excellent diastereoselectivity, propargylation afforded mixtures of diastereomers in some cases. The use of (trimethylsilyl)propargyl bromide as precursor of the Grignard reagent is necessary to avoid the formation of undesired allene derivatives. DFT calculations explain, within the experimental error, the observed behavior. Cycloaddition of the obtained pyrrolidinyl alkynes with sugar azides derived from β-(1,3)-glucans provides glycomimetics suitable to be used against fungal transglycosylases.

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37

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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38

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

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

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Kale, Mohan B., Shrikant B. Jagtap, and Santosh S. Devkate. "Study of CuSCN Catalyzed Conjugate Addition Reactions of Grignard Reagents to Substituted Chalcones with Dilithium Tetrachloromanganate and their Biological Activities." Asian Journal of Organic & Medicinal Chemistry 6, no. 2 (2021): 141–47. http://dx.doi.org/10.14233/ajomc.2021.ajomc-p327.

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The regioselective 1,4-addition reactions of copper thiocyanate catalyzed Grignard reagents to the substituted chalcones are reported. The homogeneous solution of dilithium tetrachloromanganate is used to transmetallate magnesium by using manganese. It adds regio-selectively to substituted chalcone derivatives and forms 1,4-addition products with higher yield under nitrogen atmosphere and at a lower temperature. It have been observed that manganese from dilithium tetrachloromanganate reagent replaces magnesium from Grignard reagent and adds regioselectively by 1,4-addition manner utilizing copper thiocyanate as a catalyst. The course of the reaction in the absence of dilithium tetrachloromanganate reagent was also studied and obtained a mixture of 1,2-addition and 1,4-addition products. In presence of dilithium tetrachloromanganate reagent, a good regio-selectivity and higher yield of desired 1,4-addition product were obtained. All the synthesized compounds were also evaluated for their antibacterial activity against Staphylococcus aureus (Gram-positive), Escherichia coli (Gramnegative) and antifungal activity against Aspergillus niger.

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Boldrini, Cosimo, and Syuzanna R. Harutyunyan. "Pd-catalyzed allylative dearomatisation using Grignard reagents." Chemical Communications 57, no. 89 (2021): 11807–10. http://dx.doi.org/10.1039/d1cc05609c.

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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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42

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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43

Wei, Yi-Ming, Xiao-Di Ma, Lei Wang, and Xin-Fang Duan. "Iron-catalyzed stereospecific arylation of enol tosylates using Grignard reagents." Chemical Communications 56, no. 7 (2020): 1101–4. http://dx.doi.org/10.1039/c9cc09522e.

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44

Niwa, Yasuki, Kazuki Takayama, and Makoto Shimizu. "Iminomalonate as a Convenient Electrophilic Amination Reagent for Grignard Reagents." Bulletin of the Chemical Society of Japan 75, no. 8 (August 2002): 1819–25. http://dx.doi.org/10.1246/bcsj.75.1819.

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Cicco, Luciana, Stefania Sblendorio, Rosmara Mansueto, Filippo M. Perna, Antonio Salomone, Saverio Florio, and Vito Capriati. "Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans." Chemical Science 7, no. 2 (2016): 1192–99. http://dx.doi.org/10.1039/c5sc03436a.

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46

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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Maier, Manuel C., René Lebl, Philipp Sulzer, Josef Lechner, Torsten Mayr, Matej Zadravec, Eyke Slama, et al. "Development of customized 3D printed stainless steel reactors with inline oxygen sensors for aerobic oxidation of Grignard reagents in continuous flow." Reaction Chemistry & Engineering 4, no. 2 (2019): 393–401. http://dx.doi.org/10.1039/c8re00278a.

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Tang, Jinpeng, Yu Tang, Jun Yang, and Yuanming Zhang. "Selenium-Promoted Homocoupling of Grignard Reagents." Chinese Journal of Organic Chemistry 33, no. 5 (2013): 1010. http://dx.doi.org/10.6023/cjoc201212030.

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Beckmann, Jens, and Alexandra Schütrumpf. "Thermal epimerization of diastereomeric Grignard reagents." Org. Biomol. Chem. 7, no. 1 (2009): 41–42. http://dx.doi.org/10.1039/b819178f.

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50

Hoffmann, Reinhard W. "The quest for chiral Grignard reagents." Chemical Society Reviews 32, no. 4 (2003): 225. http://dx.doi.org/10.1039/b300840c.

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