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Volumn , Issue 6, 2009, Pages 929-932

Synthesis of tetrasubstituted furans via sequential Pd(OAc) 2/Zn(OTf)2-catalyzed oxidation and cydization of aromatic alkynes with molecular oxygen

Author keywords

Aromatic alkynes; Cyclization; Oxidation; Palladium catalyzed; Synthesis; Tetrasubstituted furans

Indexed keywords

ALKYNE DERIVATIVE; AROMATIC COMPOUND; FURAN DERIVATIVE; OXYGEN; PALLADIUM;

EID: 63849105276     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088216     Document Type: Article
Times cited : (26)

References (44)
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    • (f) Friedrichsen, W. Furans and Benzo Derivatives: Synthesis, In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 351-394.
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    • 2 as eluent.
    • 2 as eluent.
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    • Spectroscopic Data for Tetrasubstituted Furans 2,3,4,5-Tetrakis(4- methoxyphenyl)furan13 Mp 206-208 °C. 1H NMR (400 MHz, CDCl3, 5, 3.78 (s, 12 H, 6.77 (d, J, 6.4 Hz, 4 H, 6.79 (d, J, 7.2 Hz, 4 H, 7.04 (d, J, 8.8 Hz, 4 H, 7.42 (d, J, 9.2 Hz, 4 H) ppm. 13CNMR(100 MHz,CDCl3, 5, 125.1, 125.8, 127.1, 127.3, 128.3, 128.5, 130.4, 130.9, 133.1, 147.7 ppm. MS (EI, 70 eV, m/z, 492 (28, M, 318 (100, 275 (31, 135 (47, 2,3,4,5-Tetrakis(4-fluorophenyl)furan14 1H NMR (400 MHz, CDCl3, 5, 6.93 (m, 8 H, 7.05-7.08 (m, 4 H, 7.41-7.44 (m, 4 H) ppm. 13C NMR (100 MHz, CDCl3, δ, 115.6 (t, J, 80 Hz, 123.5, 126.7, 127.6, 127.7, 128.6, 131.9, 147.1, 160.9, 163.4 ppm. MS (EI, 70 eV, m/z, 444 (100, M, 321 (73, 123 (69, 95 (55, 2,3,4,5-Tetrakis[4-(trifluoromethyl)phenyl]furan13
    • +], 309 (21), 119 (65), 91 (18).
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    • 2 as eluent to give 2a in 72% yield.
    • 2 as eluent to give 2a in 72% yield.
  • 34
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    • +], 178 (9), 105 (100), 77 (43).
    • +], 178 (9), 105 (100), 77 (43).
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    • The formation of 1,4-dione from tetraphenylcyclobutadienenickel and palladium complex, see: (a) Eisch, J. 1; Galle, J. E.; Aradi, A. A.; Boleslawski, M. P. J. Organomet. Chem. 1986, 312, 399.
    • The formation of 1,4-dione from tetraphenylcyclobutadienenickel and palladium complex, see: (a) Eisch, J. 1; Galle, J. E.; Aradi, A. A.; Boleslawski, M. P. J. Organomet. Chem. 1986, 312, 399.
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    • For selected examples on cyclocondensation of 1,4- dicarbonyl compounds to synthesize furans, see: a
    • For selected examples on cyclocondensation of 1,4- dicarbonyl compounds to synthesize furans, see: (a) Yin, G.; Wang, Z.; Chen, A.; Gao, M.; Wu, A.; Pan, Y. J. Org. Chem. 2008, 73, 3377.
    • (2008) J. Org. Chem , vol.73 , pp. 3377
    • Yin, G.1    Wang, Z.2    Chen, A.3    Gao, M.4    Wu, A.5    Pan, Y.6
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    • Krepski, L. R.; Heilmann, S. M.; Rasmussen, J. K.; Tumey, M. L.; Smith, H. K. II Synth. Commun. 1986, 16, 377.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.