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Volumn 10, Issue 13, 2008, Pages 2689-2692

Base-mediated cyclization reaction of 2-alkynylphenylphosphine oxides: Synthesis and photophysical properties of benzo[b]phosphole oxides

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EID: 56049105062     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800841v     Document Type: Article
Times cited : (96)

References (98)
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    • (b) Gribble, G. W. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Ed Pergamon Press: Oxford UK, 1996; Vol. 2, p 207.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 207
    • Gribble, G.W.1
  • 60
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    • The synthesis of benzo[c]phosphole has also been reported: (a) Chan, T. H.; Nwe, K. T. Tetrahedron Lett. 1973, 48, 4815.
    • The synthesis of benzo[c]phosphole has also been reported: (a) Chan, T. H.; Nwe, K. T. Tetrahedron Lett. 1973, 48, 4815.
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    • Recent examples for extended fused π-conjugated compounds: (a) Takimiya, K.; Ebata, H.; Sakamoto, K.; Uzawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604.
    • Recent examples for extended fused π-conjugated compounds: (a) Takimiya, K.; Ebata, H.; Sakamoto, K.; Uzawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604.
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    • Very recently bisphosphoryl-bridged stilbenes have been reported: (a) Fukazawa, A. ; Hara, M.; Okamoto, T.; Son, E.-C.; Xu, C.; Tamao, K.; Yamaguchi, S. Org. Lett. 2008, 10, 913.
    • Very recently bisphosphoryl-bridged stilbenes have been reported: (a) Fukazawa, A. ; Hara, M.; Okamoto, T.; Son, E.-C.; Xu, C.; Tamao, K.; Yamaguchi, S. Org. Lett. 2008, 10, 913.
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    • After the submission of this manuscript we have known that Nakamura et al. have reported the synthesis of benzo[b]phospholes by BuLi-mediated cyclization of (2-alkynylphenyl)phosphine: (a) Tsuji, H.; Sato, K.; Ilies, L.; Itoh, Y.; Sato, Y.; Nakamura, E. Org. Lett. 2008, 10, 2263-2265.
    • After the submission of this manuscript we have known that Nakamura et al. have reported the synthesis of benzo[b]phospholes by BuLi-mediated cyclization of (2-alkynylphenyl)phosphine: (a) Tsuji, H.; Sato, K.; Ilies, L.; Itoh, Y.; Sato, Y.; Nakamura, E. Org. Lett. 2008, 10, 2263-2265.
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    • The metal-catalyzed intermolecular cyclization of P-OH to alkynes has been reported: (a) Peng, A.-Y.; Ding, Y.-X. J. Am. Chem. Soc. 2003, 125, 15006.
    • The metal-catalyzed intermolecular cyclization of P-OH to alkynes has been reported: (a) Peng, A.-Y.; Ding, Y.-X. J. Am. Chem. Soc. 2003, 125, 15006.
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    • We also examined the base-mediated cyclization reaction of phenyl-(2-phenylethynylphenyl)phosphine. The reaction gave the corresponding benzo[b]phosphole in 54% isolated yield together with its oxide in 12% yield
    • We also examined the base-mediated cyclization reaction of phenyl-(2-phenylethynylphenyl)phosphine. The reaction gave the corresponding benzo[b]phosphole in 54% isolated yield together with its oxide in 12% yield.
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    • 16d We found the reaction time depends on the substrate. For example, the reaction of 2d proceeded with ca. 50% conversion for 7 h, but the reaction of 4 completes in 2 h.
    • 16d We found the reaction time depends on the substrate. For example, the reaction of 2d proceeded with ca. 50% conversion for 7 h, but the reaction of 4 completes in 2 h.
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    • 31P NMR spectra.
    • 31P NMR spectra.
  • 97
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    • 31P NMR. See Supporting Information.
    • 31P NMR. See Supporting Information.
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    • The isomer ratio could not be estimated because of the overlap of the NMR chemical shifts. An attempt to separate these isomers from each other using chromatography also failed
    • The isomer ratio could not be estimated because of the overlap of the NMR chemical shifts. An attempt to separate these isomers from each other using chromatography also failed.


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