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Journal articles on the topic 'Grignard reagents. Organomagnesium compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

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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2

Matsubara, Hiroshi, Yuki Niwa, and Ryosuke Matake. "A Grignard-Type Phase-Vanishing Method: Generation of Organomagnesium Reagent and Its Subsequent Addition to Carbonyl Compounds." Synlett 26, no. 09 (March 30, 2015): 1276–80. http://dx.doi.org/10.1055/s-0034-1380381.

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3

Matsubara, Hiroshi, Yuki Niwa, and Ryosuke Matake. "ChemInform Abstract: A Grignard-Type Phase-Vanishing Method: Generation of Organomagnesium Reagent and Its Subsequent Addition to Carbonyl Compounds." ChemInform 46, no. 39 (September 2015): no. http://dx.doi.org/10.1002/chin.201539047.

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4

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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5

Dzhemilev, U. M., A. G. Ibragimov, and G. A. Tolstikov. "Synthesis and transformations of “non-grignard” organomagnesium reagents obtained from 1,3-dienes." Journal of Organometallic Chemistry 406, no. 1-2 (March 1991): 1–47. http://dx.doi.org/10.1016/0022-328x(91)83169-5.

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6

Inoue, Atsushi, Junichi Kondo, Hiroshi Shinokubo, and Koichiro Oshima. "Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds." Chemistry - A European Journal 8, no. 7 (April 2, 2002): 1730–40. http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6.

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7

Gilman, Henry, Edith L. St. John, Nina B. St. John, and Myrl Lichtenwalter. "Relative reactivities of organometallic compounds. XI Grignard reagents." Recueil des Travaux Chimiques des Pays-Bas 55, no. 7 (September 3, 2010): 577–85. http://dx.doi.org/10.1002/recl.19360550708.

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8

Knochel, Paul, Matthias A. Schade, Sebastian Bernhardt, Georg Manolikakes, Albrecht Metzger, Fabian M. Piller, Christoph J. Rohbogner, and Marc Mosrin. "Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents." Beilstein Journal of Organic Chemistry 7 (September 13, 2011): 1261–77. http://dx.doi.org/10.3762/bjoc.7.147.

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In this review we summarize the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein. Experimental details are given for the most important reactions in the Supporting Information File 1 of this article.

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9

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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10

Alberti, Angelo, Massimo Benaglia, Dante Macciantelli, Massimo Marcaccio, Antonio Olmeda, Gian Franco Pedulli, and Sergio Roffia. "Reactions between Grignard Reagents and Thiocarbonyl Compounds: A Revisitation." Journal of Organic Chemistry 62, no. 18 (September 1997): 6309–15. http://dx.doi.org/10.1021/jo9708001.

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11

WESTERHAUSEN, M. "Heavy Grignard reagents—Synthesis and reactivity of organocalcium compounds." Coordination Chemistry Reviews 252, no. 15-17 (August 2008): 1516–31. http://dx.doi.org/10.1016/j.ccr.2007.10.023.

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12

Inoue, Atsushi, Junichi Kondo, Hiroshi Shinokubo, and Koichiro Oshima. "ChemInform Abstract: Reactions of gem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds." ChemInform 33, no. 32 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200232063.

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13

Kaino, Makoto, Kazuaki Ishihara, and Hisashi Yamamoto. "Chiral Aryl Grignard Reagents-Generation and Reactions with Carbonyl Compounds." Bulletin of the Chemical Society of Japan 62, no. 11 (November 1989): 3736–38. http://dx.doi.org/10.1246/bcsj.62.3736.

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14

Bartolo, Nicole, Jacquelyne Read, Elizabeth Valentín, and K. Woerpel. "Reactions of Allylmagnesium Halides with Carbonyl Compounds: Reactivity, Structure, and Mechanism." Synthesis 49, no. 15 (June 28, 2017): 3237–46. http://dx.doi.org/10.1055/s-0036-1588427.

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The additions of allylmagnesium reagents to carbonyl compounds are important methods in synthetic organic chemistry, but the mechanisms of these reactions are likely to be distinct from mechanisms followed by other organomagnesium reagents. Additions to alkyl aldehydes and ketones are likely to be concerted, proceeding through six-membered-ring transition states. These highly reactive reagents appear to react at rates that approach the diffusion limit, so chemoselectivity is generally low. Furthermore, reactions of allylmagnesium halides with carbonyl compounds are unlikely to follow stereochemical models that require differentiation between competing transition states. This Short Review discusses the current state of understanding of these reactions, including the structure of the reagent and unique aspects of the reactivity of allylmagnesium reagents.1 Introduction2 Reactions with Carbonyl Compounds2.1 Reactivity of Allylmagnesium Halides2.2 Selectivity of Addition3 Structure of Allylmagnesium Reagents3.1 Schlenk Equilibrium and Aggregation3.2 Spectroscopic Studies3.3 X-ray Crystallographic Studies3.4 Computational Studies of Structure4 Reaction Mechanism4.1 Substrate-Dependent Mechanisms4.2 Concerted Mechanisms4.3 Single-Electron Transfer Mechanisms4.4 Open, SE2′-Like Transition State4.5 Computational Studies of Mechanism5 Conclusion

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15

Riva, E., S. Gagliardi, M. Martinelli, D. Passarella, D. Vigo, and A. Rencurosi. "Reaction of Grignard reagents with carbonyl compounds under continuous flow conditions." Tetrahedron 66, no. 17 (April 2010): 3242–47. http://dx.doi.org/10.1016/j.tet.2010.02.078.

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16

Al Dulayymi, Juma’a R., Mark S. Baird, Ivan G. Bolesov, Alexey V. Nizovtsev, and Viacheslav V. Tverezovsky. "Hydrodehalogenation of 1,1-dibromocyclopropanes by Grignard reagents promoted by titanium compounds †." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (2000): 1603–18. http://dx.doi.org/10.1039/a910317l.

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17

Bartolo, Nicole D., and K. A. Woerpel. "Mechanistic Insight into Additions of Allylic Grignard Reagents to Carbonyl Compounds." Journal of Organic Chemistry 83, no. 17 (August 6, 2018): 10197–206. http://dx.doi.org/10.1021/acs.joc.8b01430.

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18

ALBERTI, A., M. BENAGLIA, D. MACCIANTELLI, M. MARCACCIO, A. OLMEDA, G. F. PEDULLI, and S. ROFFIA. "ChemInform Abstract: Reactions Between Grignard Reagents and Thiocarbonyl Compounds: A Revisitation." ChemInform 29, no. 2 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199802054.

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19

Yamazaki, Shoko, and Shinichi Yamabe. "A Computational Study on Addition of Grignard Reagents to Carbonyl Compounds." Journal of Organic Chemistry 67, no. 26 (December 2002): 9346–53. http://dx.doi.org/10.1021/jo026017c.

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20

Safont, Vicent S., Vicente Moliner, Mónica Oliva, Raquel Castillo, Juán Andrés, Florenci González, and Miguel Carda. "A Theoretical Study of Addition of Organomagnesium Reagents to Chiral α-Alkoxy Carbonyl Compounds." Journal of Organic Chemistry 61, no. 10 (January 1996): 3467–75. http://dx.doi.org/10.1021/jo952197x.

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21

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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22

Verenka, Ihor, and Marian Gorichko. "Recyclization reactions of 8,10-dibromocamphor with Grignard and organolithium compounds." French-Ukrainian Journal of Chemistry 9, no. 1 (2021): 97–103. http://dx.doi.org/10.17721/fujcv9i1p97-103.

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Grignard reagents and organolithium compounds react with 8,10-dibromocamphor to afford substituted 1-methyl-2-methylenebicyclo[3.2.0]heptanes. Recyclization proceeds via intramolecular enolate alkylation and Grob fragmentation of the reaction intermediates. All compounds have been characterized by 1H, 13C and 19F NMR spectroscopy and their chemical composition proved by HRMS analyses. The relative spatial arrangement of substituents in the molecule of (1-methyl-2-methylenebicyclo[3.2.0]heptan-6-yl)diphenylmethanol was studied by NOESY experiments.

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23

Bartolo, Nicole D., and K. A. Woerpel. "Evidence against Single-Electron Transfer in the Additions of Most Organomagnesium Reagents to Carbonyl Compounds." Journal of Organic Chemistry 85, no. 12 (May 14, 2020): 7848–62. http://dx.doi.org/10.1021/acs.joc.0c00481.

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24

Allef, Petra, and Horst Kunz. "Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-induced Asymmetric Addition of Organometallic Compounds to Imines." Zeitschrift für Naturforschung B 64, no. 6 (June 1, 2009): 646–52. http://dx.doi.org/10.1515/znb-2009-0609.

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Activation of imines of aromatic aldehydes by N-glycosylation with O-pivaloyl-galactopyranosyl bromide (pivalobromogalactose) and subsequent addition of organotin, organolithium, Grignard, or organozinc reagents afforded α-arylalkylamines with moderate to high diastereoselectivity.

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25

Zhong, Weihui, Yaotiao Wu, and Xingxian Zhang. "Efficient chemoselective addition of Grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran." Journal of Chemical Research 2009, no. 6 (June 1, 2009): 370–73. http://dx.doi.org/10.3184/030823409x460939.

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26

Westerhausen, Matthias, Martin Gärtner, Reinald Fischer, Jens Langer, Lian Yu, and Markus Reiher. "Heavy Grignard Reagents: Challenges and Possibilities of Aryl Alkaline Earth Metal Compounds." Chemistry - A European Journal 13, no. 22 (July 27, 2007): 6292–306. http://dx.doi.org/10.1002/chem.200700558.

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27

Schenk, C., M. L. Beekes, and Th J. de Boer. "C-Nitroso compounds. Part XXXIII. Reaction of α-chloronitrosoadamantane with Grignard reagents." Recueil des Travaux Chimiques des Pays-Bas 99, no. 7-8 (September 2, 2010): 246–52. http://dx.doi.org/10.1002/recl.19800990707.

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28

Fujiu, Motohiro, Kazuyuki Negishi, Jie Guang, Paul G. Williard, Shigeki Kuroki, and Koichi Mikami. "Chemo-, regio-, and stereo-selective perfluoroalkylations by a Grignard complex with zirconocene." Dalton Transactions 44, no. 45 (2015): 19464–68. http://dx.doi.org/10.1039/c5dt03039k.

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The unique reactivity and high selectivity of the zirconocene-hybridized heterobimetallic perfluoalkyl Grignard reagents can be employed for efficient and highly selective nucleophilic perfluoroalkylation of carbonyl compounds and epoxides, in particular.

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29

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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30

Cahiez, Ge´rard, and Blandine Laboue. "Organomanganese (II) reagents XXIII: Manganese-catalyzed acylation of organomagnesium compounds by car☐ylic acid chlorides." Tetrahedron Letters 33, no. 31 (July 1992): 4439–42. http://dx.doi.org/10.1016/s0040-4039(00)60104-1.

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31

Krasovskiy, Arkady, Felix Kopp, and Paul Knochel. "Soluble Lanthanide Salts (LnCl3⋅2 LiCl) for the Improved Addition of Organomagnesium Reagents to Carbonyl Compounds." Angewandte Chemie International Edition 45, no. 3 (January 9, 2006): 497–500. http://dx.doi.org/10.1002/anie.200502485.

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32

Kimura, Tsutomu. "Recent Advances in Magnesium Carbenoid Chemistry." Synthesis 49, no. 23 (September 12, 2017): 5105–19. http://dx.doi.org/10.1055/s-0036-1590894.

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Magnesium carbenoids are a class of organomagnesium species possessing a halo group at the α-position. The reactions of magnesium carbenoids can be classified into the following three categories: nucleophilic reactions resembling Grignard reagents, electrophilic reactions resembling organic halides, and rearrangements resembling carbenes. This short review summarizes recent studies on magnesium carbenoids reported between 2010 and 2016, and milestone studies reported before 2010 according to the classification of the reactions into the aforementioned three categories.1 Introduction2 Structures of Magnesium Carbenoids3 Reactions of Magnesium Carbenoids as Nucleophiles3.1 Nucleophilic Reactions of Magnesium Carbenoids3.2 Nucleophilic Reactions of Magnesium Alkylidene Carbenoids3.3 Nucleophilic Reactions of Cyclopropylmagnesium Carbenoids4 Electrophilic Reactions of Magnesium Carbenoids4.1 Reactions with Nucleophiles Followed by Electrophiles4.2 Reactions with Nucleophiles Possessing Electrophilic Functional Groups4.3 Nucleophilic Substitution Followed by β-Elimination5 Rearrangements of Magnesium Carbenoids5.1 1,2-Shifts of Magnesium Carbenoids5.2 1,3-C–H Insertions of Magnesium Carbenoids5.3 1,5-C–H Insertions of Magnesium Carbenoids5.4 [2+1] Cycloaddition of a Magnesium Carbenoid6 Conclusion and Outlook

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33

Imamoto, Tsuneo, Nobuyuki Takiyama, Kimikazu Nakamura, Toshihiko Hatajima, and Yasuo Kamiya. "Reactions of carbonyl compounds with Grignard reagents in the presence of cerium chloride." Journal of the American Chemical Society 111, no. 12 (June 1989): 4392–98. http://dx.doi.org/10.1021/ja00194a037.

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34

Jaumier, Pascale, Bernard Jousseaume, and Mohammed Lahcini. "Transmetalation of Tetraalkynyltin Compounds with Grignard Reagents: Access to Mono- and Dialkyltin Products." Angewandte Chemie International Edition 38, no. 3 (February 1, 1999): 402–4. http://dx.doi.org/10.1002/(sici)1521-3773(19990201)38:3<402::aid-anie402>3.0.co;2-c.

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35

Riva, E., S. Gagliardi, M. Martinelli, D. Passarella, D. Vigo, and A. Rencurosi. "ChemInform Abstract: Reaction of Grignard Reagents with Carbonyl Compounds under Continuous Flow Conditions." ChemInform 41, no. 36 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.201036065.

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36

Dong, Zhi-Bing, and Jin-Quan Chen. "Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions." Synthesis 52, no. 24 (November 4, 2020): 3714–34. http://dx.doi.org/10.1055/s-0040-1706550.

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AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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37

CAHIEZ, G., and B. LABOUE. "ChemInform Abstract: Organomanganese(II) Reagents. Part 23. Manganese-Catalyzed Acylation of Organomagnesium Compounds by Carboxylic Acid Chlorides." ChemInform 23, no. 52 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199252121.

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38

Collados, Juan F., Ricard Solà, Syuzanna R. Harutyunyan, and Beatriz Maciá. "Catalytic Synthesis of Enantiopure Chiral Alcohols via Addition of Grignard Reagents to Carbonyl Compounds." ACS Catalysis 6, no. 3 (February 19, 2016): 1952–70. http://dx.doi.org/10.1021/acscatal.5b02832.

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39

Kanai, Motomu, Yuichi Nakagawa, and Kiyoshi Tomioka. "Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds." Tetrahedron 55, no. 13 (March 1999): 3843–54. http://dx.doi.org/10.1016/s0040-4020(99)00095-2.

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40

Boudin, Alain, Geneviève Cerveau, Claude Chuit, Robert J. P. Corriu, and Catherine Reye. "Reaction of Grignard Reagents with Dianionic Hexacoordinated Silicon Complexes: Organosilicon Compounds from Silica Gel." Angewandte Chemie International Edition in English 25, no. 5 (May 1986): 474–76. http://dx.doi.org/10.1002/anie.198604741.

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41

Samuel, Mini S., Kim M. Baines, and Donald W. Hughes. "The photolysis of Si,Si-di-tert-butyltetramesitylsiladigermirane in the presence of methylmagnesium iodide." Canadian Journal of Chemistry 78, no. 11 (November 1, 2000): 1474–78. http://dx.doi.org/10.1139/v00-058.

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The photolysis of Si,Si-di-tert-butyltetramesitylsiladigermirane in the presence of methylmagnesium iodide at 15°C has been investigated. Five products were isolated and identified from the complex product mixture: mesityldimethylgermane, dimesitylmethylgermane, (di-tert-butylmethylsilyl)mesitylmethylgermane, meta-(di-tert-butylmethylsilyl)toluene, and para-(di-tert-butylmethylsilyl)toluene. The characterization of these compounds and proposed mechanisms for their formation will be discussed.Key words: germasilene, Grignard reagents, germylmagnesium compounds.

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42

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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43

Goncalves-Contal, Sylvie, Ludovic Gremaud, Laëtitia Palais, Lucille Babel, and Alexandre Alexakis. "Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents." Synthesis 48, no. 19 (June 28, 2016): 3301–8. http://dx.doi.org/10.1055/s-0035-1562487.

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β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C–C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

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44

Jaumier, Pascale, Bernard Jousseaume, and Mohammed Lahcini. "ChemInform Abstract: Transmetalation of Tetraalkynyltin Compounds with Grignard Reagents: Access to Mono- and Dialkyltin Products." ChemInform 30, no. 24 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199924181.

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45

Haynes, RK, SC Vonwiller, JP Stokes, and LM Merlino. "The Preparation of Some β-Sulfonylacrylate Thioesters and β-Sulfonylvinyl Ketones." Australian Journal of Chemistry 41, no. 6 (1988): 881. http://dx.doi.org/10.1071/ch9880881.

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β- Sulfonylacrylate phenyl and t-butyl thioesters , and β- sulfonylvinyl ketones have been prepared by oxidation of the corresponding β-aryl- and β-alkyl- thio compounds. In one case the β- sulfonylvinyl ketone was obtained from an epoxy sulfone . The β-aryl- and β-alkyl- thio compounds were obtained by chlorination- dehydrochlorination of saturated precursors. The reactions of 3-( phenylthio ) propionyl chloride with organocadmium and Grignard reagents were used to prepare some of the saturated precursors of the β- sulfonylvinyl ketones.

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46

Boukattaya, Fatma, Amal Daoud, Fabien Boeda, Morwenna S. M. Pearson-Long, Néji Gharsallah, Adel Kadri, Philippe Bertus, and Houcine Ammar. "Synthesis and Biological Evaluation of 3-cyano-4H-chromene Derivatives Bearing Carbamate Functionality." Medicinal Chemistry 15, no. 3 (April 12, 2019): 257–64. http://dx.doi.org/10.2174/1573406414666181009124449.

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Background: 2-Aminochromene derivatives display important pharmacological properties, including mainly antibiotic and anticancer activities. Objective: The study aims to synthesize new chromene derivatives via a new approach using Grignard reagents, for the evaluation of their antibiotic and antifungal properties. Method: A series of novel 3-cyano-4-aminochromene derivatives bearing alkyl substituents at the 4-position was prepared for biological evaluation. Results: These compounds were obtained by the addition of various Grignard reagents into Nethoxycarbonyl- 3-cyanoiminocoumarines in moderate to good yields (72-96%). The reaction is completely regioselective. The new chromene derivatives were screened for their in vitro antimicrobial activities against a panel of six bacterial and three fungal strains using agar dilution method. Conclusion: The antibacterial activity of the chromene derivatives was more pronounced on Gram-positive bacteria than on Gram-negative bacteria with a significant activity observed against Staphylococcus aureus. An interesting antifungal activity against Fusarium sp. and Fusarium oxysporum was also noticed.

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47

Salehi, Peyman, Maryam Mohebbi, Morteza Bararjanian, Samad Ebrahimi, and Martin Smieško. "Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis: Highly Enantioselective Addition of Diethylzinc to Aldehydes." Synthesis 50, no. 09 (February 5, 2018): 1841–48. http://dx.doi.org/10.1055/s-0037-1609224.

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Noscapine, a natural alkaloid, has never been used as a parent scaffold in chiral induction. The first examples of noscapinoid compounds as efficient catalysts in asymmetric synthesis are now reported. Three derivatives of noscapine were synthesized from its reaction with different Grignard reagents. Asymmetric addition of diethylzinc to aldehydes was performed in the presence of these catalysts in high yields and good to excellent ees.

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48

Kulinkovich, O. G. "Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds." Pure and Applied Chemistry 72, no. 9 (January 1, 2000): 1715–19. http://dx.doi.org/10.1351/pac200072091715.

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Dialkoxytitanacyclopropane intermediates [or titanium (II)-olefin complexes] generated in situ from ethylmagnesium bromide and titanium (IV) isopropoxide react with allylic alcohols and allylic ethers to afford SN2' allylic ethylation products. The reaction proceeds with high regioselectivity and with low to high trans-/cis-stereoselectivity. This observation and others suggest a reaction mechanism involving an EtMgBr-initiated formation of titanacyclopentane ate complex 10 from titanacyclopropane-olefin complex 7 as a key step. Based on this assumption, a modified mechanism of titanium-mediated cyclopropanation of esters with Grignard reagents is proposed.

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49

Dowson, G. R. M., I. Dimitriou, R. E. Owen, D. G. Reed, R. W. K. Allen, and P. Styring. "Kinetic and economic analysis of reactive capture of dilute carbon dioxide with Grignard reagents." Faraday Discussions 183 (2015): 47–65. http://dx.doi.org/10.1039/c5fd00049a.

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Carbon Dioxide Utilisation (CDU) processes face significant challenges, especially in the energetic cost of carbon capture from flue gas and the uphill energy gradient for CO₂reduction. Both of these stumbling blocks can be addressed by using alkaline earth metal compounds, such as Grignard reagents, as sacrificial capture agents. We have investigated the performance of these reagents in their ability to both capture and activate CO₂directly from dried flue gas (essentially avoiding the costly capture process entirely) at room temperature and ambient pressures with high yield and selectivity. Naturally, to make the process sustainable, these reagents must then be recycled and regenerated. This would potentially be carried out using existing industrial processes and renewable electricity. This offers the possibility of creating a closed loop system whereby alcohols and certain hydrocarbons may be carboxylated with CO₂and renewable electricity to create higher-value products containing captured carbon. A preliminary Techno-Economic Analysis (TEA) of an example looped process has been carried out to identify the electrical and raw material supply demands and hence determine production costs. These have compared broadly favourably with existing market values.

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Murahashi, Shun-Ichi. "Palladium-catalyzed cross-coupling reaction of organic halides with Grignard reagents, organolithium compounds and heteroatom nucleophiles." Journal of Organometallic Chemistry 653, no. 1-2 (July 2002): 27–33. http://dx.doi.org/10.1016/s0022-328x(02)01167-1.

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