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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.
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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.
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Two other approaches to diarylmethanes have been reported. See: a
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33751157939
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For cross-coupling of an in situ generated organoborane with a substituted benzyl chloride, see
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(a) McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391.
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19
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15044361090
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Benzylic carbonates have been employed in Suzuki-Miyaura crosscouplings. See
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Benzylic carbonates have been employed in Suzuki-Miyaura crosscouplings. See: Kuwano. R.; Yokogi, M. Org. Lett. 2005, 7, 945.
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23
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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
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2 has a trans-geometry. This material was used in all of the examples presented in this paper.
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24
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(a) Fairlamb, I. J. S.; Kapdi, A. R.; Lynam, J. M.; Taylor, R. J. K.; Whitwood, A. C. Tetrahedron 2004, 60, 5711.
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26
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(c) Serrano, J. L.; Fairlamb, I. J. S.; Sánchez, G.; García, L.; Pérez, J.; Vives, J.; López, G.; Crawforth, C. M.; Taylor, R. J. K. Eur. J. Inorg. Chem. 2004, 2706.
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Taylor, R.J.K.9
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(d) Crawforth, C. M.; Fairlamb, I. J. S.; Kapdi, A. R.; Serrano, J. L.; Taylor, R. J. K.; Sanchez, G. Adv. Synth. Catal. 2006, 348, 405.
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(f) Fairlamb, I. J. S.; Taylor, R. J. K.; Serrano, J. L.; Sanchez, G. New J. Chem. 2006, 30, 1685.
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38349178536
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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
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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.
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31
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2; it is clear that both are useful precatalysts for coupling benzylic halide components in this reaction.
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2; it is clear that both are useful precatalysts for coupling benzylic halide components in this reaction.
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32
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38349142702
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Commercial sources of furan-2-boronic acid and thiophene-2-boronic acid were found to degrade at 25°C in the presence of moisture.
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Commercial sources of furan-2-boronic acid and thiophene-2-boronic acid were found to degrade at 25°C in the presence of moisture.
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34
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2042507954
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For Suzuki-Miyaura cross-couplings using allylic halides, see: a
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For Suzuki-Miyaura cross-couplings using allylic halides, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
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Miyaura, N.1
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0346786657
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and references cited therein
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(b) Suzuki, A. J. Organomet. Chem. 1998, 576, 147, and references cited therein.
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Suzuki, A.1
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36
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0000564666
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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.
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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.
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(c) Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829.
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Lakmini, H.5
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39
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38349186059
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Many monosubstituted aryl bromides and arylboronic acids effectively cross couple in good yields using the generic reaction conditions
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Many monosubstituted aryl bromides and arylboronic acids effectively cross couple in good yields using the generic reaction conditions.
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40
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4143073526
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6527. PEO with a molecular weight of 100 000 was employed in this study
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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.
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Nobre, S.M.1
Wolke, S.I.2
da Rosa, R.G.3
Monteiro, A.L.4
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41
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Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F.; Sánchez, G.; López, G.; Serrano, J. L.; García, L.; Pérez, J.; Pérez, E. Dalton Trans. 2004, 3970.
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Dalton Trans
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Fairlamb, I.J.S.1
Kapdi, A.R.2
Lee, A.F.3
Sánchez, G.4
López, G.5
Serrano, J.L.6
García, L.7
Pérez, J.8
Pérez, E.9
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42
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38349169991
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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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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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