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Volumn 47, Issue 21, 2008, Pages 4019-4022

Fluorescent naphthyl- and anthrylazoles from the catalytic coupling of phenylazoles with internal alkynes through the cleavage of multiple C-H bonds

Author keywords

C C coupling; C H activation; Fluorescent solids; Homogeneous catalysis; Rhodium

Indexed keywords

CHEMICAL REACTIONS; COPPER; DERIVATIVES; DIFFERENCE EQUATIONS; FLUORESCENCE; HYDROCARBONS; LIGHT EMISSION; LUMINESCENCE; RHODIUM;

EID: 47049108951     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800924     Document Type: Article
Times cited : (382)

References (55)
  • 1
    • 53549130069 scopus 로고    scopus 로고
    • Selected reviews: a J. E. Anthony, Angew. Chem. 2008, 120, 460;
    • Selected reviews: a) J. E. Anthony, Angew. Chem. 2008, 120, 460;
  • 20
    • 0031797589 scopus 로고    scopus 로고
    • For a review on polyphenylated benzenes, see: h
    • For a review on polyphenylated benzenes, see: h) M. Müller, C. Kübel, K. Müllenm, Chem. Eur. J. 1998, 4, 2099.
    • (1998) Chem. Eur. J , vol.4 , pp. 2099
    • Müller, M.1    Kübel, C.2    Müllenm, K.3
  • 21
    • 53549129561 scopus 로고    scopus 로고
    • For application to electroluminescence devices, see: i, Japanese Patent JP 2005302657
    • For application to electroluminescence devices, see: i) K. Enomoto, T. Chiba, Japanese Patent JP 2005302657, 2005;
    • (2005)
    • Enomoto, K.1    Chiba, T.2
  • 22
    • 53549108669 scopus 로고    scopus 로고
    • Japanese Patent JP 2003027048
    • j) T. Igarashi, X. Qiu, Japanese Patent JP 2003027048, 2003.
    • (2003)
    • Igarashi, T.1    Qiu, X.2
  • 23
    • 19944426813 scopus 로고    scopus 로고
    • The polyvinylation by palladium-catalyzed cross-coupling with hexa- and octabromoarenes was reported: B. Stulgies, P. Prinz, J. Magull, K. Rauch, K. Meindl, S. RLhl, A. de Meijere, Chem. Eur. J. 2005, 11, 308
    • The polyvinylation by palladium-catalyzed cross-coupling with hexa- and octabromoarenes was reported: B. Stulgies, P. Prinz, J. Magull, K. Rauch, K. Meindl, S. RLhl, A. de Meijere, Chem. Eur. J. 2005, 11, 308.
  • 24
    • 53549130335 scopus 로고    scopus 로고
    • The overall yield of decaphenylanthracene when prepared by using the Diels-Alder procedure was reported to be only 0.1, whereas that of octaphenylnaphthalene was 26, See reference [4g
    • The overall yield of decaphenylanthracene when prepared by using the Diels-Alder procedure was reported to be only 0.1%, whereas that of octaphenylnaphthalene was 26%. See reference [4g].
  • 28
    • 38949161093 scopus 로고    scopus 로고
    • Recently, polyarylated and partially fluorinated aromatics were synthesized by using the coupling of polyfluorinated aromatic substrates with 1,4-dilithio-1,2,3,4-tetraaryl-1,3-butadienes: d S. Li, J. Xiang, X. Mei, C. Xu, Tetrahedron Lett. 2008, 49, 1690.
    • Recently, polyarylated and partially fluorinated aromatics were synthesized by using the coupling of polyfluorinated aromatic substrates with 1,4-dilithio-1,2,3,4-tetraaryl-1,3-butadienes: d) S. Li, J. Xiang, X. Mei, C. Xu, Tetrahedron Lett. 2008, 49, 1690.
  • 29
    • 33947293932 scopus 로고    scopus 로고
    • 2: a G. M. Whitesides, W. J. Ehmann, J. Am. Chem. Soc. 1970, 92, 5625;
    • 2: a) G. M. Whitesides, W. J. Ehmann, J. Am. Chem. Soc. 1970, 92, 5625;
  • 31
    • 0041888449 scopus 로고    scopus 로고
    • X = I: c S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836;
    • X = I: c) S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836;
  • 34
    • 0037202198 scopus 로고    scopus 로고
    • X = COCl: f T. Yasukawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 12680.
    • X = COCl: f) T. Yasukawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 12680.
  • 35
    • 34447327520 scopus 로고    scopus 로고
    • 2H: g K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362.
    • 2H: g) K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362.
  • 36
    • 37549027556 scopus 로고    scopus 로고
    • 2OH: h T. Uto, M. Shimizu, K. Ueura, T. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 298.
    • 2OH: h) T. Uto, M. Shimizu, K. Ueura, T. Tsurugi, T. Satoh, M. Miura, J. Org. Chem. 2008, 73, 298.
  • 37
    • 3242705276 scopus 로고    scopus 로고
    • o-Dihalobenzenes: i W. Huang, X. Zhou, K.-I. Kanno, T. Takahashi, Org. Lett. 2004, 6, 2429.
    • o-Dihalobenzenes: i) W. Huang, X. Zhou, K.-I. Kanno, T. Takahashi, Org. Lett. 2004, 6, 2429.
  • 38
    • 33846918696 scopus 로고    scopus 로고
    • Selected reviews for C-H bond activation: a D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
    • Selected reviews for C-H bond activation: a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
  • 45
  • 47
    • 53549113999 scopus 로고    scopus 로고
    • The coupling of benzene with alkynes by using a stoichiometric amount of Pd was reported. Naphthalene yields based on Pd were less than 20%. See reference [8e].
    • The coupling of benzene with alkynes by using a stoichiometric amount of Pd was reported. Naphthalene yields based on Pd were less than 20%. See reference [8e].
  • 48
    • 0013497219 scopus 로고    scopus 로고
    • The stoichiometric reactions of some palladacycles with alkynes to give naphthalenes were reported: a J. Dupont, M. Pfeffer, M. A. Rotteveel, Organometallics 1989, 8, 1116;
    • The stoichiometric reactions of some palladacycles with alkynes to give naphthalenes were reported: a) J. Dupont, M. Pfeffer, M. A. Rotteveel, Organometallics 1989, 8, 1116;
  • 50
    • 53549102292 scopus 로고    scopus 로고
    • Reference [8d
    • c) Reference [8d].
  • 51
    • 3042704672 scopus 로고    scopus 로고
    • Catalytic functionalizations involving N-directed C-H activation of 2-phenylpyrazoles have been reported. Acylation: a T. Asaumi, T. Matsuo, T. Fukuyama, Y. Ie, F. Kakiuchi, N. Chatani, J. Org. Chem. 2004, 69, 4433;
    • Catalytic functionalizations involving N-directed C-H activation of 2-phenylpyrazoles have been reported. Acylation: a) T. Asaumi, T. Matsuo, T. Fukuyama, Y. Ie, F. Kakiuchi, N. Chatani, J. Org. Chem. 2004, 69, 4433;
  • 53
    • 53549127626 scopus 로고    scopus 로고
    • Arylation: c L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;
    • Arylation: c) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.