PDF herunterladen
Synlett 2013; 24(3): 355-358
DOI: 10.1055/s-0032-1317793
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Hydroarylation of Diazoacetic Ester

Igor D. Titanyuk*
Moscow State University, Department of Chemistry 119991, Leninskie Gory 1-3, Moscow, Russian Federation   Fax: +7(495)9328846   eMail: i-titan@yandex.ru
,
Irina P. Beletskaya
Moscow State University, Department of Chemistry 119991, Leninskie Gory 1-3, Moscow, Russian Federation   Fax: +7(495)9328846   eMail: i-titan@yandex.ru
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 09. November 2012

Accepted after revision: 18. Dezember 2012

Publikationsdatum:
17. Januar 2013 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

The novel procedure for the Pd-catalyzed hydroarylation of α-diazoacetic ester is reported. In the presence of a catalytic amount of PdCl2(PPh3)2 the three-component reaction of aryl ­iodides, ethyl diazoacetate, and formic acid proceeds smoothly ­resulting in the formation of a series of arylacetates.

Key words

hydroarylation - diazoacetic ester - arylacetates - ­palladium catalysis - cross-coupling

Supporting Information

    for this manuscript is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Included are spectroscopic and analytical data for key building blocks and oligosaccharides.
  • Supporting Information
 

  • References and Notes


      • For recent reviews, see:
    • 2a Zhang Y, Wang J. Eur. J. Org. Chem. 2011; 1015
    • 2b Zhang Y, Wang J. Chem. Commun. 2009; 5350
  • 3 Peng C, Cheng J, Wang J. J. Am. Chem. Soc. 2007; 129: 8708
    CrossrefSuche in Google Scholar
    • 5a Devine SK. J, Van Vranken DL. Org. Lett. 2007; 2047
    • 5b Devine SK. J, Van Vranken DL. Org. Lett. 2008; 1909
    • 5c Kadirka R, Devine SK. J, Adams CS, Van Vranken DL. Angew. Chem. Int. Ed. 2009; 48: 3677
      CrossrefPubMedSuche in Google Scholar
  • 7 Curhan SG, Eavey R, Shargorodsky J, Curhan GC. Am. J. Med. 2010; 123: 231
    CrossrefSuche in Google Scholar
  • 8 Harrington PJ, Lodewijk E. Org. Process Res. Dev. 1997; 1: 72
    CrossrefSuche in Google Scholar
  • 9 Musa KA. K, Matxain JM, Eriksson LA. J. Med. Chem. 2007; 50: 1735
    CrossrefSuche in Google Scholar
  • 10 Bandgar BP, Sarangdhar RJ, Ahamed FA, Viswakarma S. J. Med. Chem. 2011; 54: 1202
    CrossrefSuche in Google Scholar
  • 11 Adams R, Thal AF. Org. Synth., Coll. Vol. I 1941; 436
  • 12 Duan J, Jiang J, Gong J, Fan Q, Jiang D. J. Mol. Catal. A: Chem. 2000; 159: 89
    CrossrefSuche in Google Scholar
  • 13 Fructos MR, Belderrain TR, de Fremont P, Scott NM, Nolan SP, Diaz-Requejo MM, Perez PJ. Angew. Chem. Int. Ed. 2005; 44: 5284
    Suche in Google Scholar
    • 14a Hama T, Hartwig JF. Org. Lett. 2008; 1545
    • 14b Biscoe MR, Buchwald SL. Org. Lett. 2009; 1773
  • 15 Broering M, Brandt CD, Stellwag S. Chem. Commun. 2003; 2344
  • 16 Albeniz AC, Espinet P, Manrique R, Perez-Mateo A. Angew. Chem. Int. Ed. 2002; 41: 2363
    CrossrefPubMedSuche in Google Scholar
  • 17 Sole D, Vallverdu L, Solans X, Font-Bardia M, Bonjoch J. Organometallics 2004; 23: 1438
    CrossrefSuche in Google Scholar
  • 18 Typical Procedure for the Pd-Catalyzed Cross-Coupling between Aryl Iodides and EDA To a mixture of aryl iodide 1a–h (1 mmol), PdCl2(PPh3)2 (35 mg, 0.05 mmol) in a Schlenk flask under argon atmosphere, Et3N (254 mg, 2.5 mmol) and formic acid (69 mg, 1.5 mmol) in MeCN (3 mL) were added. The mixture was stirred and heated to 70 °C, then EDA (171 mg, 1.5 mmol) in MeCN (2 mL) was added in small portions for 40–60 min. The mixture was stirred at the same temperature until 1a–h disappeared (the total time of heating indicated in Table 2). The solvent was evaporated in vacuo. Purification of the mixture by column chromatography (EtOAc–hexane = 1:10 v/v) gave the pure compounds 2a–h.
  • 19 Selected Data for Synthesized Compounds Compound 2a: colorless oil. 1H NMR (400 MHz, CDCl3): δ = 7.98 (d, 2 H, J = 7.2 Hz), 7.35 (d, 2 H, J = 7.2 Hz), 4.14 (q, 2 H, J = 7.0 Hz), 3.88 (s, 3 H), 3.65 (s, 2 H), 1.23 (t, 3 H, J = 7.1 Hz). 13C NMR (100 MHz, CDCl3): δ = 170.8, 166.8, 139.3, 129.8, 129.3, 129.0, 61.0, 52.0, 41.3, 14.1. IR (film): 1733, 1615, 1290 cm–1. Anal. Calcd for C12H14O4: C, 64.85; H, 6.35. Found: C, 64.92; H, 6.39. Compound 2e: yellow oil. 1H NMR (400 MHz, CDCl3): δ = 8.14 (m, 2 H), 7.62 (m, 1 H), 7.51 (m, 1 H), 4.18 (q, 2 H, J = 7.0 Hz), 3.73 (s, 2 H), 1.27 (t, 3 H, J = 7.1 Hz). 13C NMR (100 MHz, CDCl3): δ = 170.3, 148.2, 136.0, 135.6, 129.4, 124.4, 122.2, 61.4, 41.0, 14.1. IR (film): 1740, 1540, 1360 cm–1. Anal. Calcd for C10H11NO4: C, 57.41; H, 5.30; N, 6.70. Found: C, 57.48; H, 5.39; N, 6.75. Compound 2g: colorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.52 (m, 2 H), 7.64 (d, 1 H, J = 7.8 Hz), 7.25 (m, 1 H), 4.16 (q, 2 H, J = 7.0 Hz), 3.61 (s, 2 H), 1.25 (t, 3 H, J = 7.1 Hz). 13C NMR (100 MHz, CDCl3): δ = 170.6, 150.3, 148.5, 136.7, 129.8, 128.5, 123.3, 61.1, 38.5, 14.1. IR (film): 1730, 1600 cm–1. Anal. Calcd for C9H11NO2: C, 65.44; H, 6.71; N, 8.48. Found: C, 65.54; H, 6.66; N, 8.57.