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Volumn 9, Issue 26, 2007, Pages 5397-5400

Simple palladium(II) precatalyst for suzuki-miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; PALLADIUM;

EID: 38349106240     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702291r     Document Type: Article
Times cited : (148)

References (42)
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    • (2004) Metal-catalyzed Cross-coupling Reactions
  • 2
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    • Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1.
    • (2004) Transition Metals for Organic Synthesis , vol.1
  • 7
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    • 4NBr as a stoichiometric additive, in reactions of benzylic halides and arylboronic acids, see: (a) Botella, L.; Nájera, C. J. Organomet. Chem. 2002, 663, 46.
    • 4NBr as a stoichiometric additive, in reactions of benzylic halides and arylboronic acids, see: (a) Botella, L.; Nájera, C. J. Organomet. Chem. 2002, 663, 46.
  • 9
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    • Two other approaches to diarylmethanes have been reported. See: a
    • Two other approaches to diarylmethanes have been reported. See: (a) Vanier, C.; Lorgé, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 1679
    • Vanier, C.1    Lorgé, F.2    Wagner, A.3    Mioskowski, C.4
  • 11
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    • For cross-coupling of an in situ generated organoborane with a substituted benzyl chloride, see
    • For cross-coupling of an in situ generated organoborane with a substituted benzyl chloride, see: Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1994, 59, 6501.
    • (1994) J. Org. Chem , vol.59 , pp. 6501
    • Maddaford, S.P.1    Keay, B.A.2
  • 19
    • 15044361090 scopus 로고    scopus 로고
    • Benzylic carbonates have been employed in Suzuki-Miyaura crosscouplings. See
    • Benzylic carbonates have been employed in Suzuki-Miyaura crosscouplings. See: Kuwano. R.; Yokogi, M. Org. Lett. 2005, 7, 945.
    • (2005) Org. Lett , vol.7 , pp. 945
    • Kuwano, R.1    Yokogi, M.2
  • 23
    • 38349140292 scopus 로고    scopus 로고
    • Note that cis-1 was used in these studies. The commerical source of PdBr(N-Succ)(PPh3)2 has a trans-geometry. This material was used in all of the examples presented in this paper
    • 2 has a trans-geometry. This material was used in all of the examples presented in this paper.
  • 30
    • 38349178536 scopus 로고    scopus 로고
    • In ref 15a, we reported that Pd(N-Succ)2(PPh 3)2 is an effective precatalyst for Suzuki-Miyaura cross-couplings of aryl halides with arylboronic acids. The coupling of 4-nitrobromobenzene with phenylboronic acid was tested with cis-1 as the precatalyst in this paper. For this specific example, cis-1 was less effective than Pd(N-Succ)2(PPh3)2. Since this report, it has emerged that couplings of this aryl halide, and related compounds, can be complicated by electron-transfer processes, making it a poor benchmark substrate for screening catalysts/precatalysts
    • 2. Since this report, it has emerged that couplings of this aryl halide, and related compounds, can be complicated by electron-transfer processes, making it a poor benchmark substrate for screening catalysts/precatalysts.
  • 31
    • 38349144501 scopus 로고    scopus 로고
    • 2; it is clear that both are useful precatalysts for coupling benzylic halide components in this reaction.
    • 2; it is clear that both are useful precatalysts for coupling benzylic halide components in this reaction.
  • 32
    • 38349142702 scopus 로고    scopus 로고
    • Commercial sources of furan-2-boronic acid and thiophene-2-boronic acid were found to degrade at 25°C in the presence of moisture.
    • Commercial sources of furan-2-boronic acid and thiophene-2-boronic acid were found to degrade at 25°C in the presence of moisture.
  • 34
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    • For Suzuki-Miyaura cross-couplings using allylic halides, see: a
    • For Suzuki-Miyaura cross-couplings using allylic halides, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
    • (1995) Chem. Rev , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 35
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    • and references cited therein
    • (b) Suzuki, A. J. Organomet. Chem. 1998, 576, 147, and references cited therein.
    • (1998) J. Organomet. Chem , vol.576 , pp. 147
    • Suzuki, A.1
  • 36
    • 0000564666 scopus 로고    scopus 로고
    • 2 (air) as an oxidant in homocoupling of organoboronic acids, see: (a) Smith, C. A.; Campi, E. M.; Jackson, R.; Marcuccio, S.; Naeslund, C. G. M.; Deacon, G. B. Synlett 1997, 131.
    • 2 (air) as an oxidant in homocoupling of organoboronic acids, see: (a) Smith, C. A.; Campi, E. M.; Jackson, R.; Marcuccio, S.; Naeslund, C. G. M.; Deacon, G. B. Synlett 1997, 131.
  • 39
    • 38349186059 scopus 로고    scopus 로고
    • Many monosubstituted aryl bromides and arylboronic acids effectively cross couple in good yields using the generic reaction conditions
    • Many monosubstituted aryl bromides and arylboronic acids effectively cross couple in good yields using the generic reaction conditions.
  • 40
    • 4143073526 scopus 로고    scopus 로고
    • 6527. PEO with a molecular weight of 100 000 was employed in this study
    • Nobre, S. M.; Wolke, S. I.; da Rosa, R. G.; Monteiro, A. L. Tetrahedron Lett. 2004, 45, 6527. PEO with a molecular weight of 100 000 was employed in this study.
    • (2004) Tetrahedron Lett , vol.45
    • Nobre, S.M.1    Wolke, S.I.2    da Rosa, R.G.3    Monteiro, A.L.4
  • 42
    • 38349169991 scopus 로고    scopus 로고
    • PEO acts as an organic stabilizer for in situ formed palladium colloids/nanoparticles (formed by degradation of the palladium(II) precatalyst), produced by aggregation of palladium(0).
    • PEO acts as an organic stabilizer for in situ formed palladium colloids/nanoparticles (formed by degradation of the palladium(II) precatalyst), produced by aggregation of palladium(0).


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