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Relevant bibliographies by topics / Grignard reagents. Halides

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Academic literature on the topic 'Grignard reagents. Halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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Journal articles on the topic "Grignard reagents. Halides"

1

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

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

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2

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

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

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3

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

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

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4

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

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

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5

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

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6

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

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7

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

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

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8

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

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

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9

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

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10

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

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Book chapters on the topic "Grignard reagents. Halides"

1

Evano, G. "Via Grignard Reagents." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00116.

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Zhang, M., and P. R. Hanson. "Addition of Grignard Reagents." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00782.

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3

Landelle, G., and J. F. Paquin. "Conjugate Addition of Grignard Reagents." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-120-00019.

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4

Smith, M. D. "From Grignard Reagents and Arsenic(III) Halides." In Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-004-00020.

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Avilov, D., and D. Dittmer. "Reaction of Organotellurenyl Halides with Grignard Reagents." In Ene-X Compounds (X=S, Se, Te, N, P), 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-033-00414.

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6

Young, D. "From Propargyl Grignard Reagents and Tin Halides." In Compounds of Group 14 (Ge, Sn, Pb), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-005-00529.

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O'Connor, J. M. "From Iridium Halides and Grignard or Organolithium Reagents." In Compounds with Transition Metal-Carbon pi-Bonds and Compounds of Groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os), 1. Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-001-00614.

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8

Wolkenberg, S. E., and R. M. Garbaccio. "Addition of Grignard Reagents to Chiral Dehydromorpholinones." In Three Carbon-Heteroatom Bonds: Acid Halides; Carboxylic Acids and Acid Salts, 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-020-00434.

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9

Araki, S., and T. Hirashita. "Reaction of Indium Halides with Organolithium or Grignard Reagents." In Science of Synthesis Knowledge Updates KU 2010/4, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-107-00138.

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10

Eagle, P. A. C. "From Lead(II) Chloride, Grignard Reagents, and Allyl Halides." In Compounds of Group 14 (Ge, Sn, Pb), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-005-00811.

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