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[
1] For selected reviews on Pd-catalysed Suzuki–Miyaura reac-
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D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 6046–6047;
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2
457–2483; b) S. P. Stanforth, Tetrahedron 1998, 54, 263–304;
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9
695; e) N. Miyaura, Top. Curr. Chem. 2002, 219, 11–59; f) F.
[
6] For selected Ni heterogeneously catalysed Suzuki–Miyaura
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B. H. Lipshutz, T. Butler, E. Swift, Org. Lett. 2008, 10, 697–
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1
473.
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3] For Ni-catalysed Suzuki–Miyaura aryl–aryl coupling reactions
of haloarenes using the chloride, see: a) S. Saito, M. Sakai,
N. Miyaura, Tetrahedron Lett. 1996, 37, 2993–2996; b) A. F.
Indolese, Tetrahedron Lett. 1997, 38, 3513–3516; c) S. Saito, S.
Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024–8030; d) J.-
C. Galland, M. Savignac, J.-P. Genêt, Tetrahedron Lett. 1999,
[
[
700.
1
[7] For room-temperature Suzuki–Miyaura aryl–aryl coupling re-
actions catalysed by nickel catalysts, see: a) Y. Kobayashi, R.
Mizojiri, Tetrahedron Lett. 1996, 37, 8531–8534; b) Z.-Y. Tang,
Q.-S. Hu, J. Am. Chem. Soc. 2004, 126, 3058–3059; c) Z.-Y.
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Org. Lett. 2008, 10, 4879–4882.
4
8
4
0, 2323–2326; e) K. Inada, N. Miyaura, Tetrahedron 2000, 56,
657–8660; f) C. Chen, L.-M. Yang, Tetrahedron Lett. 2007,
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[8] Prior to our reports, there was only one report of the successful
II
Tetrahedron Lett. 2007, 48, 7899–7902; using the bromide/io-
dide, see: h) N. E. Leadbeater, S. M. Resouly, Tetrahedron 1999,
use of Ni –(σ-aryl) complexes as catalysts in the cyanation of
bromothiophenes, see: J. V. Soolinger, H. D. Verkruijsse, M. A.
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Keegstra, L. Brandsma, Synth. Commun. 1990, 20, 3153–3156.
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1624–1627; d) C.-Y. Gao, X. Cao, L.-M. Yang, Org. Biomol.
Chem. 2009, 7, 3922–3925.
[
4] For Ni-catalysed Suzuki–Miyaura aryl–aryl coupling reactions
of aryl sulfonates (OTs, OBs, OMs), see: a) D. Zim, V. R.
Lando, J. Dupont, A. L. Monterio, Org. Lett. 2001, 3, 3049–
[10] For the preparation of trans-haloarylbis(triphenylphosphane)
nickel(II), see: a) L. Cassar, S. Ferrara, M. Foá, in: Advances
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5] For Ni-catalysed Suzuki–Miyaura aryl–aryl coupling reactions
of other electrophiles containing unusual leaving groups using
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Yu, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 14468–14470; b)
K. W. Quasdorf, X. Tian, N. K. Garg, J. Am. Chem. Soc. 2008,
[
[11] Note: In all experiments there always exists a small amount of
the 1-arylnaphthalene byproduct generated from the precata-
II
lyst Ni –(1-naphthyl) complex. In most cases, the byproduct
1
30, 14422–14423; using aryl carbamates, see: c) K. W. Quas-
dorf, M. Riener, K. V. Petrova, N. K. Garg, J. Am. Chem. Soc.
009, 131, 17748–17749; d) A. Antoft-Finch, T. Blackburn, V.
does not cause any difficulty in the separation of the desired
products due to pronounced differences in their R values in
f
2
chromatography. In a few cases, the byproduct may be removed
easily by recrystallization because of its low content. In the
case of the 1-naphthyl substrate, the yield reported was deter-
Snieckus, J. Am. Chem. Soc. 2009, 131, 17750–17752; e) L. Xu,
B.-J. Li, Z.-H. Wu, X.-Y. Lu, B.-T. Guan, B.-Q. Wang, K.-Q.
Zhao, Z.-J. Shi, Org. Lett. 2010, 12, 884–887; f) L. J. Gooßen,
K. Gooßen, C. Stanciu, Angew. Chem. 2009, 121, 3621; Angew.
Chem. Int. Ed. 2009, 48, 3569–3571; using aryl methyl ether,
see: g) M. Tobisu, T. Shimasaki, N. Chatani, Angew. Chem.
II
mined after subtracting the contribution from the Ni –(1-
naphthyl) complex used, based on an estimate that [(1-naphth-
yl)Ni(PPh
3
)
2
Cl] would be completely converted.
Received: November 11, 2010
Published Online: January 26, 2011
2008, 120, 4944; Angew. Chem. Int. Ed. 2008, 47, 4866–4869;
Eur. J. Org. Chem. 2011, 1467–1471
© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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