Synlett, Inhaltsverzeichnis Synlett 2015; 26(02): 259-264DOI: 10.1055/s-0034-1379612 letter © Georg Thieme Verlag Stuttgart · New York d-Glucosamine as a Green Ligand for Palladium-Catalyzed Cross-Coupling of Aryl and Heteroaryl Halides Abadh Kishor Jha Department of Chemistry, Indian Institute of Technology, Hauz Khas, Delhi-110016, India Fax: +91(11)26581102 eMail: njain@chemistry.iitd.ac.in , Rahul Kumar Shahni Department of Chemistry, Indian Institute of Technology, Hauz Khas, Delhi-110016, India Fax: +91(11)26581102 eMail: njain@chemistry.iitd.ac.in , Nidhi Jain* Department of Chemistry, Indian Institute of Technology, Hauz Khas, Delhi-110016, India Fax: +91(11)26581102 eMail: njain@chemistry.iitd.ac.in› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Naturally occurring d-glucosamine works as an efficient green alternative to phosphines in palladium-catalyzed Heck coupling of aryl and heteroaryl halides. An array of trans-stilbene derivatives, aryl naphthyl alkenes, heteroaryl olefins, and β-aryl-substituted acrylates has been synthesized in short reaction times in moderate to high yields. Key words Key wordsgreen chemistry - cross-coupling - carbohydrates - palladium - transition metals Volltext Referenzen References and Notes 1a Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417 1b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062 1c Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609 1d Molnár Á. Chem. Rev. 2011; 111: 2251 1e Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873 2 Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320 3a Albéniz AC, Espinet P, Martín-Ruiz B, Milstein D. J. Am. Chem. Soc. 2001; 123: 11504 3b Gstöttmayr CW. K, Böhm VP. W, Herdtweck E, Grosche M, Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1363 3c Reetz MT, Lohmer G, Schwickardi R. Angew. Chem. Int. 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The reaction mixture was extracted with hexane (3 × 25mL). The combined organic layers were washed with H2O, dried over Na2SO4, filtered, and concentrated under reduced pressure. Column chromatography on silica gel afforded pure products.(E)-4-(2-Naphthalen-2-ylvinyl)benzonitrile (5b)White crystalline solid. 1H NMR (300 MHz, CDCl3): δ = 7.75–780 (m, 4 H), 7.64 (d, J = 8.4 Hz, 1 H), 7.51–7.55 (m, 3 H), 7.41 (t, J = 3.9 Hz, 2 H), 7.28 (d, J = 16.2 Hz, 1 H), 7.08–7.17 (m, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 141.9, 133.8, 133.6, 133.5, 132.54, 132.50, 128.6, 128.2, 127.8, 127.7, 126.99, 126.9, 126.6, 126.5, 123.3, 119.1, 110.6 ppm. MS (EI): m/z = 256 [M + 1].(E)-2-(2-o-Tolylvinyl)naphthalene (5c)White crystalline solid. 1H NMR (300 MHz, CDCl3): δ = 7.731 (s, 2 H), 7.68–7.71 (m, 2 H), 7.64 (d, J = 8.7 Hz, 1 H), 7.54 (d, J = 6.9 Hz, 1 H), 7.34–7.38 (m, 2 H), 7.31–7.33 (m, 1 H), 7.12–7.16 (m, 1 H), 7.02–7.11 (m, 3 H), 2.36 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 136.5, 135.9, 135.2, 133.8, 133.1, 130.6, 130.1, 128.4, 128.1, 127.8, 127.7, 126.9, 126.7, 126.4, 126.3, 125.9, 125.4, 123.7, 20.1. MS (EI): m/z = 244. Zusatzmaterial Zusatzmaterial Supporting Information
