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Volumn 345, Issue 8, 2003, Pages 931-935

Suzuki-Miyaura Cross-Coupling with Quasi-Heterogeneous Palladium

Author keywords

Cross coupling; Heterogeneous catalyst; Palladium; Palladium leaching; Suzuki Miyaura

Indexed keywords

CARBON; PALLADIUM;

EID: 0242439345     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303036     Document Type: Article
Times cited : (148)

References (46)
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    • For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4009-4011
    • Zim, D.1    Monteiro, A.L.2
  • 6
    • 0001357479 scopus 로고    scopus 로고
    • For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 313-326
    • Lipshutz, B.H.1
  • 7
    • 0034616375 scopus 로고    scopus 로고
    • For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
    • (2000) Tetrahedron , vol.56 , pp. 2139-2144
    • Lipshutz, B.H.1    Sclafani, J.A.2    Blomgren, P.A.3
  • 8
    • 0000728442 scopus 로고    scopus 로고
    • For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
    • (1997) J. Org. Chem. , vol.62 , pp. 8024-8030
    • Saito, S.1    Oh-tani, S.2    Miyaura, N.3
  • 9
    • 0000894049 scopus 로고    scopus 로고
    • For nickel-catalyzed reactions, see: a) D. Zim, A. L. Monteiro, Tetrahedron Lett. 2002, 43, 4009-4011; b) B. H. Lipshutz, Adv. Synth. Catal. 2001, 343, 313-326; c) B. H. Lipshutz, J. A. Sclafani, P. A. Blomgren, Tetrahedron 2000, 56, 2139-2144; d) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; e) D. Zim, R. L. Vanusa, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049-3051.
    • (2001) Org. Lett. , vol.3 , pp. 3049-3051
    • Zim, D.1    Vanusa, R.L.2    Dupont, J.3    Monteiro, A.L.4
  • 10
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    • note
    • [5]), however, chelating phosphines such as dppf can be used.
  • 11
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    • note
    • 3500 ppm of palladium and 1160 ppm of iron.
  • 36
    • 0242486019 scopus 로고    scopus 로고
    • note
    • We found that many commercial samples of Pd/C were catalysts for this cross-coupling. We used a dry, 5% Pd/C (C6064) from Engelhard and water wet 5% Pd/C (A405023-5) and 10% Pd/C (A402032-10) catalysts from Johnson Matthey in this study.
  • 39
    • 0242570015 scopus 로고    scopus 로고
    • note
    • [6d] Our sample filtration would not remove these nanosized Pd particles, however, in the same paper they report that these Pd colloids undergo quantitative oxidative-addition by stoichiometric iodobenzene. In our system, the bromoquinoline 1 concentration is always greater than the palladium concentration which would make the presence of palladium nanoparticles unlikely.
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    • Initially, the increase in Pd concentration follows the increase in the coupled product 3. We do not feel that the product 3 is causing the solubilization of the Pd because the Pd level goes through a maximum and then decreases when the concentration of 3 is the greatest. Also, heteroatoms that coordinate to transition metals often retard the cross-coupling reaction. Additionally, no N-coordinated Pd complexes were observed during an ESI-MS study of the Suzuki-Miyaura cross-coupling of pyridyl halides; see: A. O. Aliprantis, J. W. Canary, J. Am. Chem. Soc. 1994, 116, 6985-6986.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6985-6986
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    • note
    • [10] concluded during their study of the Heck reaction that leaching and redeposition of supported Pd occured and that the concentration of Pd was related to the concentration of starting materials.
  • 46
    • 0242570017 scopus 로고    scopus 로고
    • note
    • 2K, however, preliminary NMR studies indicate that the reaction of boronic acid 2 with KF generates 6 species; L. M. DiMichele, unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.