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Volumn 3, Issue 10, 2001, Pages 1555-1557

Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium

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EID: 0000138940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015850d     Document Type: Article
Times cited : (324)

References (46)
  • 7
    • 0346786657 scopus 로고    scopus 로고
    • Reviews of Suzuki Coupling: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.1
  • 30
  • 32
    • 0041705546 scopus 로고    scopus 로고
    • note
    • 1H NMR were identical to authentic samples.
  • 33
    • 0042707143 scopus 로고    scopus 로고
    • note
    • A small amount of biphenyl identified in the reaction correlates with the number of surface palladium atoms and suggests that the phenylboronic acid plays a role in reducing the surface palladium. Thus, reactions are performed with a 20% excess of aryl boronic acid.
  • 35
    • 0041705551 scopus 로고    scopus 로고
    • note
    • (b) Postreaction NMR of the ethanol solvent revealed a complex mixture including the presence of aldehydic protons (δ 9.74, q, J = 2.5 Hz) indicating oxidation of ethanol.
  • 39
    • 24844469003 scopus 로고
    • Work function is defined as the minimum work that must be done to remove an electron from the metal at 0 K. See: (a) Lang, N. D.; Kohn, W. Phys. Rev. B 1971, 3, 1215-1223.
    • (1971) Phys. Rev. B , vol.3 , pp. 1215-1223
    • Lang, N.D.1    Kohn, W.2
  • 41
    • 0028261953 scopus 로고
    • This is analogous to the acceleration of oxidative addition of aryl chlorides to Pd(0) via coordination of an electron-withdrawing tricarbonylchromium group to the arene ring. See: Uemura, M.; Nishimura, H.; Kamikawa, K.; Nakayama, K.; Hayashi, Y. Tetrahedron Lett. 1994, 35, 1909-1912.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 1909-1912
    • Uemura, M.1    Nishimura, H.2    Kamikawa, K.3    Nakayama, K.4    Hayashi, Y.5
  • 43
    • 0005642368 scopus 로고
    • For the reaction of p-chloronitrobenzene with phenylboronic acid at 80°C with 5 mol % of Pd/C, after filtration through 0.45 mm filter, we found 1.0 ppm of palladium by atomic absorption spectroscopy. If the reaction were to occur exclusively on palladium that leached into solution, a turnover number (TON) of 16 000 would be required. Catalytic palladium-catalyzed cross-couplings with TON greater than 10000 have only been demonstrated in few cases ((a) Murray, W. V. Chemtracts-Org. Chem. 1993, 6, 263-284.
    • (1993) Chemtracts-Org. Chem. , vol.6 , pp. 263-284
    • Murray, W.V.1
  • 45
    • 0023628245 scopus 로고
    • (c) Williams, D.; Kannan, R. J. Org. Chem. 1987, 52, 5435-5437) and those which utilize aryl chlorides to the best of our knowledge are nonexistent.
    • (1987) J. Org. Chem. , vol.52 , pp. 5435-5437
    • Williams, D.1    Kannan, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.