Zhen Ma , Atash V. Gurbanov , Abel M. Maharramov , Firudin I. Guseinov , Maximilian N. Kopylovich , Fedor I. Zubkov , Kamran T. Mahmudov , Armando J.L. Pombeiro
{"title":"铜(II)芳基腙配合物对水中Henry反应中CH活化的催化作用","authors":"Zhen Ma , Atash V. Gurbanov , Abel M. Maharramov , Firudin I. Guseinov , Maximilian N. Kopylovich , Fedor I. Zubkov , Kamran T. Mahmudov , Armando J.L. Pombeiro","doi":"10.1016/j.molcata.2016.05.030","DOIUrl":null,"url":null,"abstract":"<div><p>Three new water-soluble copper(II) complexes [Cu(HL)(H<sub>2</sub>O){(CH<sub>3</sub>)<sub>2</sub>NCHO}] (<strong>1</strong>), [Cu(H<sub>2</sub>L)<sub>2</sub>(im)<sub>4</sub>]·CH<sub>3</sub>OH (<strong>2</strong>) and [Cu(HL)(CH<sub>3</sub>OH)]<sub>2</sub>(<em>μ</em><sub>2</sub>-py) (<strong>3</strong>) were synthesized from copper(II) nitrate and sodium (<em>Z</em>)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzene-sulfonate (NaH<sub>2</sub>L), in the absence (for <strong>1</strong>) and presence of imidazole (im) (for <strong>2</strong>) or pyrazine (py) (for <strong>3</strong>), and fully characterized. The complexes <strong>1–3</strong> have been tested as stereoselective C<img>H activating catalysts for the model nitroaldol (Henry) condensation of nitroethane with various aldehydes in water. <strong>1</strong> was the most active catalyst affording 64−87% yields with <em>syn/anti</em> diasteroselectivities up to 77:23.</p></div>","PeriodicalId":370,"journal":{"name":"Journal of Molecular Catalysis A: Chemical","volume":null,"pages":null},"PeriodicalIF":5.0620,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.molcata.2016.05.030","citationCount":"48","resultStr":"{\"title\":\"Copper(II) arylhydrazone complexes as catalysts for CH activation in the Henry reaction in water\",\"authors\":\"Zhen Ma , Atash V. Gurbanov , Abel M. Maharramov , Firudin I. Guseinov , Maximilian N. Kopylovich , Fedor I. Zubkov , Kamran T. Mahmudov , Armando J.L. Pombeiro\",\"doi\":\"10.1016/j.molcata.2016.05.030\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Three new water-soluble copper(II) complexes [Cu(HL)(H<sub>2</sub>O){(CH<sub>3</sub>)<sub>2</sub>NCHO}] (<strong>1</strong>), [Cu(H<sub>2</sub>L)<sub>2</sub>(im)<sub>4</sub>]·CH<sub>3</sub>OH (<strong>2</strong>) and [Cu(HL)(CH<sub>3</sub>OH)]<sub>2</sub>(<em>μ</em><sub>2</sub>-py) (<strong>3</strong>) were synthesized from copper(II) nitrate and sodium (<em>Z</em>)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzene-sulfonate (NaH<sub>2</sub>L), in the absence (for <strong>1</strong>) and presence of imidazole (im) (for <strong>2</strong>) or pyrazine (py) (for <strong>3</strong>), and fully characterized. The complexes <strong>1–3</strong> have been tested as stereoselective C<img>H activating catalysts for the model nitroaldol (Henry) condensation of nitroethane with various aldehydes in water. <strong>1</strong> was the most active catalyst affording 64−87% yields with <em>syn/anti</em> diasteroselectivities up to 77:23.</p></div>\",\"PeriodicalId\":370,\"journal\":{\"name\":\"Journal of Molecular Catalysis A: Chemical\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.0620,\"publicationDate\":\"2017-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.molcata.2016.05.030\",\"citationCount\":\"48\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Molecular Catalysis A: Chemical\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1381116916302126\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Catalysis A: Chemical","FirstCategoryId":"1","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1381116916302126","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Copper(II) arylhydrazone complexes as catalysts for CH activation in the Henry reaction in water
Three new water-soluble copper(II) complexes [Cu(HL)(H2O){(CH3)2NCHO}] (1), [Cu(H2L)2(im)4]·CH3OH (2) and [Cu(HL)(CH3OH)]2(μ2-py) (3) were synthesized from copper(II) nitrate and sodium (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazinyl)benzene-sulfonate (NaH2L), in the absence (for 1) and presence of imidazole (im) (for 2) or pyrazine (py) (for 3), and fully characterized. The complexes 1–3 have been tested as stereoselective CH activating catalysts for the model nitroaldol (Henry) condensation of nitroethane with various aldehydes in water. 1 was the most active catalyst affording 64−87% yields with syn/anti diasteroselectivities up to 77:23.
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The Journal of Molecular Catalysis A: Chemical publishes original, rigorous, and scholarly full papers that examine the molecular and atomic aspects of catalytic activation and reaction mechanisms in homogeneous catalysis, heterogeneous catalysis (including supported organometallic catalysis), and computational catalysis.
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