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Heterogeneous Palladium Catalyst
COMMUNICATION
3557–3560; b) R. Akiyama, S. Kobayashi, Angew. Chem. 2001, 113,
3577–3579; Angew. Chem. Int. Ed. 2001, 40, 3469–3471; c) N. Bre-
meyer, S. V. Lay, C. Ramarao, I. M. Shirley, S. C. Smith, Synlett
2002, 1843–1844; d) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115,
204–207; Angew. Chem. Int. Ed. 2003, 42, 194–197; e) K. Okamoto,
R. Akiyama, S. Kobayashi, J. Org. Chem. 2004, 69, 2871–2873; f) R.
Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412–3413;
g) S. V. Ley, C. Mitchell, D. Pears, C. Ramarao, J.-Q. Yu, W. Zhou,
Org. Lett. 2003, 5, 4665–4668; h) K. Okamoto, R. Akiyama, S. Ko-
bayashi, Org. Lett. 2004, 6, 1987–1990; i) R. Nakao, H. Rhee, Y.
Uozumi, Org. Lett. 2005, 7, 163–165; j) K. Okamoto, R. Akiyama,
H. Yoshida, T. Yoshida, S. Kobayashi, J. Am. Chem. Soc. 2005, 127,
2125–2135; k) A. Corma, H. Garcia, A. Leyva, J. Mol. Catal. A
2005, 230, 97–105; l) H. Hagio, M. Sugiura, S. Kobayashi, Org. Lett.
2006, 8, 375–378; m) Y. Uozumi, T. Suzuka, R. Kawade, H. Takena-
ka, Synlett 2006, 2109–2113; n) Y. Nakai, T. Kimura, Y. Uozumi,
Synlett 2006, 3065–3068; o) Y. Uozumi, R. Nakao, H. Rhee, J. Orga-
nomet. Chem. 2007, 692, 420–427; p) H. Oyamada, R. Akiyama, H.
Hagio, T. Naito, S. Kobayashi, Chem. Commun. 2006, 4297–4299;
q) Y. M. A. Yamada, T. Arakawa, H. Hocke, Y. Uozumi, Angew.
Chem. 2007, 119, 718–720; Angew. Chem. Int. Ed. 2007, 46, 704–
706.
gawa, Y. Monguchi, H. Sajiki, Chem. Commun. 2007, 5069–5071;
f) H. Sakurai, T. Tsukuda, T. Hirao, J. Org. Chem. 2002, 67, 2721–
2722; g) T. Tagata, M. Nishida, J. Org. Chem. 2003, 68, 9412–9415;
h) M. Lysꢃn, K. Kçhler, Synlett 2005, 1671–1674; i) M. Lysꢃn, K.
Kçhler, Synthesis 2006, 692–698; j) A. Cassez, A. Ponchel, F.
Hapiot, E. Monflier, Org. Lett. 2006, 8, 4823–4826; k) J. P. Simeone,
J. R. Sowa, Jr., Tetrahedron 2007, 63, 12646–12654; l) S. Mori, T.
Yanase, S. Aoyagi, Y. Monguchi, T. Maegawa, H. Sajiki, Chem. Eur.
J. 2008, 14, 6994–6999; m) Y. Monguchi, K. Kitamoto, T. Ikawa, T.
Maegawa, H. Sajiki, Adv. Synth. Catal. 2008, 350, 2767–2777.
[11] a) T. Adachi, S. Ando, J. Watanabe, J. Chromatogr. A 2002, 944, 41–
com/Index_E.htm
[12] a) H. Sajiki, T. Ikawa, K. Hirota, Tetrahedron Lett. 2003, 44, 171–
174; b) H. Sajiki, T. Ikawa, K. Hirota, Tetrahedron Lett. 2003, 44,
4837–4839; c) T. Ikawa, H. Sajiki, K. Hirota, Tetrahedron 2005, 61,
2217–2231; d) T. Ikawa, H. Sajiki, K. Hirota, J. Synth. Org. Chem.
Jpn. 2005, 63, 1218–1231; e) Y. Kitamura, A. Tanaka, M. Sato, K.
Oono, T. Ikawa, T. Maegawa, Y. Monguchi, H. Sajiki, Synth.
Commun. 2007, 37, 4381–4388.
[13] Although X-ray electron spectroscopy (XPS) of the complex could
not be measured, owing to the charge-up arising from its insulation,
the powder X-ray diffraction (XRD) analysis indicated that most of
palladium species exist as palladium(0) metal (see the Supporting
Information).
[7] B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam, B. Sreed-
har, J. Am. Chem. Soc. 2002, 124, 14127–14136.
[8] S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation
for Organic Synthesis, Wiley, New York, 2001.
[14] Inductively coupled plasma (ICP) analysis determined that
9.90 wt% palladium was contained in the complex.
[9] For reviews: a) M. Seki, J. Syn. Org. Chem. Jpn. 2006, 64, 853–866;
b) M. Seki, Synthesis 2006, 2975–2992; c) F.-X. Felpin, T. Ayad, S.
Mitra, Eur. J. Org. Chem. 2006, 2679–2690.
[15] S. Kobayashi, S. Nagayama, J. Am Chem. Soc. 1998, 120, 2985–2986.
[16] DIAION HP20 originally contained 55–65% (w/w) of water, but it
was removed during the preparation.
[10] a) H. Sajiki, T. Kurita, A. Kozaki, G. Zhang, Y. Kitamura, T. Maega-
wa, K. Hirota, J. Chem. Res. 2004, 593–595; Erratum: H. Sajiki, T.
Kurita, A. Kozaki, G. Zhang, Y. Kitamura, T. Maegawa, K. Hirota,
J. Chem. Res. 2005, 344; b) H. Sajiki, T. Kurita, A. Kozaki, G.
Zhang, Y. Kitamura, T. Maegawa, K. Hirota, Synthesis 2005, 537–
542; Erratum: H. Sajiki, T. Kurita, A. Kozaki, G. Zhang, Y. Kita-
mura, T. Maegawa, K. Hirota, Synthesis 2005, 852; c) T. Maegawa,
Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi,
K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, H. Sajiki,
Chem. Eur. J. 2007, 13, 5937–5943; d) Y. Kitamura, A. Sakurai, T.
Udzu, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2007, 63,
10596–10602; e) Y. Kitamura, S. Sako, T. Udzu, A. Tsutsui, T. Mae-
[17] a) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117,
4516–4563; Angew. Chem. Int. Ed. 2005, 44, 4442–4489; b) A.
Suzuki, Proc. Jpn Acad. Ser. B 2004, 80, 359–371; c) J. Hassan, M.
Sꢃvignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102,
1359–1469; d) S. Kotha, S. Lahiri, D. Kashinath, Tetrahedron 2002,
58, 9633–9695.
[18] Only two examples of the hetero-Suzuki–Miyaura reactions that use
the heterogeneous Pd/C catalyst have recently been reported.[10e,19]
[19] M. S. McClure, E. Roschangar, S. J. Hodson, A. Millar, M. H. Os-
terhout, Synthesis 2007, 1682–1685.
Received: September 26, 2008
Published online: December 15, 2008
Chem. Eur. J. 2009, 15, 834 – 837
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