Synlett, Inhaltsverzeichnis Synlett 2018; 29(14): 1875-1880DOI: 10.1055/s-0037-1609558 letter © Georg Thieme Verlag Stuttgart · New YorkPalladium-Catalyzed Arylation of Aromatic Amides Directed by a [4-Chloro-2-(1H-pyrazol-1-yl)phenyl]amine Auxiliary Autoren Institutsangaben Ya-Hua Hu ◊ School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn Zhi Xu ◊ School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn Ling-Yan Shao School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn Ya-Fei Ji* School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) ◊ Ya-Hua Hu and Zhi Xu are equal first authors. Abstract A palladium-catalyzed ortho-arylation of aromatic amides directed by [4-chloro-2-(1H-pyrazol-1-yl)phenyl]amine as a bidentate auxiliary has been established. The reaction is characterized by normal working conditions, a broad substrate scope, and a wide functional-group tolerance. In particular, the protocol is compatible with highly sterically demanding ortho-substituted anilides and aryl iodide partners, with good yields. Key words Key wordsC–H activation - arylation - amides - directing groups - palladium catalysis - biaryls Volltext Referenzen References and Notes 1a Kakiuchi F. Murai S. Acc. Chem. Res. 2002; 35: 826 1b Godula K. Sames D. Science 2006; 312: 67 1c Chen X. Engle KM. Wang D.-H. Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094 1d Lyons TM. Sanford MS. Chem. 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The filtrate was washed with EtOAc (3 × 15 mL) and the organic layers were combined, dried (MgSO4), and concentrated in vacuo to provide a crude product that was purified by column chromatography [silica gel, PE–EtOAc (40:1)] to give the desired product 3 or 4. N-[4-Chloro-2-(1H-pyrazol-1-yl)phenyl]-4′-methoxy-3-methylbiphenyl-2-carboxamide (3f) Yellow oil; yield: 106 mg (85%). 1H NMR (400 MHz, CDCl3): δ = 9.94 (s, 1 H), 8.43 (d, J = 8.8 Hz, 1 H), 7.57 (d, J = 1.6 Hz, 1 H), 7.54 (d, J = 2.8 Hz, 1 H), 7.33 (t, J = 7.6 Hz, 1 H), 7.30 (dd, J 1 = 8.0, J 2 = 2.4 Hz, 1 H), 7.19–7.23 (m, 3 H), 7.19 (d, J = 4.0 Hz, 1 H), 7.17 (d, J = 8.4 Hz, 1 H), 6.70 (d, J = 8.8 Hz, 2 H), 6.39 (t, J = 2.4 Hz, 1 H), 3.73 (s, 3 H), 2.40 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 168.5, 158.7, 141.5 (2 C), 138.9, 136.4, 135.5, 132.5, 130.0, 129.9, 129.8, 129.4 (2 C), 129.2, 129.1, 127.7, 127.4, 124.4, 122.5, 113.7 (2 C), 107.5, 55.2, 19.5. 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The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. 14a Lapointe D. Fagnou K. Chem. Lett. 2010; 39: 1118 14b Balcells D. Clot E. Eisenstein O. Chem. Rev. 2010; 110: 749 14c Musaev DG. Figg TM. Kaledin AL. Chem. Soc. Rev. 2014; 43: 5009 15a Weibel J.-M. Blanc A. Pale P. Chem. Rev. 2008; 108: 3149 15b Arroniz C. Denis JG. Ironmonger A. Rassias G. Larrosa I. Chem. Sci. 2014; 5: 3509 Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
