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Volumn 133, Issue 20, 2011, Pages 7719-7721

Ni-catalyzed ketene cycloaddition: A system that resists the formation of decarbonylation side products

Author keywords

[No Author keywords available]

Indexed keywords

DECARBONYLATIONS; SIDE PRODUCTS;

EID: 79957704469     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2007627     Document Type: Article
Times cited : (55)

References (49)
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    • Chem. Soc. Rev.
    • Domínguez, G.1    Pérez-Castells, J.2
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    • Ketenes were coupled with alkynes using a Rh catalyst. However, products arising from a β-hydride elimination step were obtained. See
    • Ketenes were coupled with alkynes using a Rh catalyst. However, products arising from a β-hydride elimination step were obtained. See: Kondo, T.; Niimi, M.; Yoshida, Y.; Wada, K.; Mitsudo, T.; Kimura, Y.; Toshimitsu, A. Molecules 2010, 15, 4189
    • (2010) Molecules , vol.15 , pp. 4189
    • Kondo, T.1    Niimi, M.2    Yoshida, Y.3    Wada, K.4    Mitsudo, T.5    Kimura, Y.6    Toshimitsu, A.7
  • 18
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    • For an excellent review of the interactions of ketenes with various metals, see
    • For an excellent review of the interactions of ketenes with various metals, see: Geoffery, G. L.; Bassner, S. L. Adv. Organomet. Chem. 1988, 28, 1
    • (1988) Adv. Organomet. Chem. , vol.28 , pp. 1
    • Geoffery, G.L.1    Bassner, S.L.2
  • 19
    • 0000375666 scopus 로고
    • For various metal-ketene complexes, see: Ni
    • For various metal-ketene complexes, see: Ni: Hoberg, H.; Korff, J. J. Organomet. Chem. 1978, 152, 255
    • (1978) J. Organomet. Chem. , vol.152 , pp. 255
    • Hoberg, H.1    Korff, J.2
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    • In; Wiley-Interscience: New York.
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    • Tidwell, T.T.1
  • 36
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    • For a complementary approach to cyclohexadienones and phenols, see
    • For a complementary approach to cyclohexadienones and phenols, see: Tang, P. C.; Wulff, W. D. J. Am. Chem. Soc. 1984, 106, 1132
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 1132
    • Tang, P.C.1    Wulff, W.D.2
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    • For natural products containing a 2,4-cyclohexadienone core, see
    • For natural products containing a 2,4-cyclohexadienone core, see: Kaouadji, M. J. Nat. Prod. 1986, 49, 500
    • (1986) J. Nat. Prod. , vol.49 , pp. 500
    • Kaouadji, M.1
  • 42
    • 79957773837 scopus 로고    scopus 로고
    • When DPPF was employed as the ligand in the cycloaddition of other substrates, such as diynes 5 and 7 with a, a complex mixture of products that included diyne dimer, ketene dimer, and cycloadduct was formed, hampering purification. In general, reactions run with DPPB were cleaner. Therefore, our optimized conditions employed DPPB as the ligand of choice
    • When DPPF was employed as the ligand in the cycloaddition of other substrates, such as diynes 5 and 7 with a, a complex mixture of products that included diyne dimer, ketene dimer, and cycloadduct was formed, hampering purification. In general, reactions run with DPPB were cleaner. Therefore, our optimized conditions employed DPPB as the ligand of choice.
  • 46
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    • When 3-hexyne and phenyl ethyl ketene (a) were subjected to the optimized conditions, the cycloaddition product was not obtained. Instead, only ketene dimerization was observed by GC
    • When 3-hexyne and phenyl ethyl ketene (a) were subjected to the optimized conditions, the cycloaddition product was not obtained. Instead, only ketene dimerization was observed by GC.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.