Nanocrystalline Magnesium Oxide Stabilized Palladium(0): An Efficient Reusable Catalyst
Chemistry, ACS Monograph Series, American Chemis-
try Society: Washington DC, 1990, p 174; c) M. B.
Smith, in: Organic Synthesis, McGraw-Hill, Singapore,
1994, p 221; d) R. C. Larock, in: Comprehensive Organ-
ic Transformations: A Guide to Functional Group Prep-
arations, 2nd edn., Wiley-VCH, New York, 1999, p 2583;
e) J. March, March’s Advanced Organic Chemistry: Re-
actions, Mechanisms and Structure, 5th edn., Wiley-In-
terscience, New York, 2007.
479–482; f) H. Wu, Q. Zhang, Y. Wang, Adv. Synth.
Catal. 2005, 347, 1356; g) N. Kakiuchi, Y. Maeda, T.
Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
h) M. Hayashi, K. Yamada, S. Nakayama, H. Hayashi,
S. Yamazaki, Green Chem. 2000, 2, 257; i) T. Nishimura,
N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun.
2000, 1245.
[8] G. Ann, H. Ahn, K. A. De Castro, H. Rhee, Synthesis
2010, 477.
[4] For a discussion of atom economy in organic synthesis
see: a) B. M. Trost, Science 1991, 254, 1471; b) B. M.
Trost, Angew. Chem. 1995, 107, 285; Angew. Chem. Int.
Ed. Engl. 1995, 34, 259.
[9] a) J. Chen, Q. Zhang, Y. Wang, H. Wan, Adv. Synth.
Catal. 2008, 350, 453; b) U. R. Pillai, E. Sahle-Demes-
sie, Green Chem. 2004, 6, 161; c) F. Li, Q. Zhang, Y.
Wang, Appl. Catal. A: Gen. 2008, 334, 217; d) H. Wu,
Q. Zhang, Y. Wang, Adv. Synth. Catal. 2005, 347, 1356;
e) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204;
Angew. Chem. Int. Ed. 2003, 42, 194; f) M. S. Kwon, N.
Kim, C. M. Park, J. S. Lee, K. Y. Kang, J. Park, Org.
Lett. 2005, 7, 1077.
[10] a) M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M.
Choudary, Adv. Synth. Catal. 2005, 347, 2002; b) M. L.
Kantam, S. Roy, M. Roy, M. S. Subhas, P. R. Likhar, B.
Sreedhar, B. M. Choudary, Synlett 2006, 2747; c) M. L.
Kantam, R. Chakravarti, U. Pal, B. Sreedhar, S. Bhar-
gava, Adv. Synth. Catal. 2008, 350, 822; d) M. L.
Kantam, R. Chakravarti, C. V. Reddy, B. Sreedhar, S.
Bhargava, Adv. Synth. Catal. 2008, 350, 2544.
[5] For references on homogeneous palladium catalysts for
aerobic oxidation of alcohols see: a) K. Kaneda, Y.
Fujii, K. Morioka, J. Org. Chem. 1996, 61, 4502; b) K.
Kaneda, Y. Fujii, K. Ebitani, Tetahedron Lett. 1997, 38,
9023; c) K. P. Peterson, R. C. Larock, J. Org. Chem.
1998, 63, 3185; d) T. Nishimura, T. Onoue, K. Ohe, S.
Uemura, Tetahedron Lett. 1998, 39, 6011; e) T. Nishi-
mura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem.
1999, 64, 6750; f) G. Brink, I. W. C. E. Arends, R. A.
Sheldon, Science 2000, 287, 1636; g) K. Hallman, C.
Moberg, Adv. Synth. Catal. 2001, 343, 260; h) M. J.
Schultz, C. C. Park, M. S. Sigman, Chem. Commun.
2002, 3034; i) D. R. Jensen, M. J. Schultz, J. A. Mueller,
M. S. Sigman, Angew. Chem. 2003, 115, 3940; Angew.
Chem. Int. Ed. 2003, 42, 3810; j) G. Brink, I. W. C. E.
Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344,
355; k) T. Nishimura, S. Uemura, Synlett 2004, 201; l) S.
Paavola, K. Zetterberg, T. Privalov, I. Csoregh, C.
Moberg, Adv. Synth. Catal. 2004, 346, 237; m) T. Iwasa-
wa, M. Tokunaga, Y. Obora, Y. Tsuji, J. Am. Chem.
Soc. 2004, 126, 6554; n) M. J. Schultz, S. S. Hamilton,
D. R. Jensen, M. S. Sigman, J. Org. Chem. 2005, 70,
3343. For references on heterogeneous palladium cata-
lysts for aerobic oxidation of alcohols, see: o) T. Nishi-
mura, N. Kakiuchi, M. Inoue, S. Uemura, Chem.
Commun. 2000, 1245; p) N. Kakiuchi, Y. Maeda, T.
Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620;
q) K. Moroi, K. Yamaguchi, T. Hara, T. Mizugaki, K.
Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124,
11572; r) D. R. Jensen, M. J. Schutz, J. A. Mueller,
M. S. Sigman, Angew. Chem. 2003, 115, 3940; Angew.
Chem. Int. Ed. 2003, 42, 3810; s) K. Mori, T. Hara, T.
Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc.
2004, 126, 10657; t) M. S. Kwon, N. Kim, C. M. Park,
J. S. Lee, K. Y. Kang, J. Park, Org. Lett. 2005, 7, 1077;
u) U. R. Pillai, E. Sahle-Demessie, Green Chem. 2004,
6, 161; v) B. Karimi, A. Zamani, J. H. Clark, Organo-
metallics 2005, 24, 4695.
[11] a) P. Jeevanandam, K. J. Klabunde, Langmuir 2002, 18,
5309; b) K. J. Klabunde, R. Mulukutla, Nanoscale Ma-
terials in Chemistry, Wiley Interscience, New York,
2001, Chapter 7, p 23.
[12] For various reactions catalyzed by NAP-MgO see:
a) M. L. Kantam, U. Pal, B. Sreedhar, B. M. Choudary,
Adv. Synth. Catal. 2007, 349, 1671; b) M. L. Kantam,
K. V. S. Ranganath, K. Mahendar, L. Chakrapani, B. M.
Choudary, Tetrahedron Lett. 2007, 48, 7646; c) B. M.
Choudary, M. L. Kantam, K. V. S. Ranganath, K. Ma-
hendar, B. Sreedhar, J. Am. Chem. Soc. 2004, 126,
3396; d) B. M. Choudary, K. V. S. Ranganath, U. Pal,
M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2005,
127, 13167; e) M. L. Kantam, K. Mahender, S. Bharga-
va, J. Chem. Sci. 2010, 122, 63; f) M. L. Kantam, L.
Chakrapani, B. M. Choudary, Synlett 2008, 1946.
[13] M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M.
Choudary, Adv. Synth. Catal. 2005, 347, 2002.
[14] H. P. Choo, K. Y. Liew, H. Liu, J. Mater. Chem. 2002,
12, 934.
[15] a) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K.
Ebitani, K, Kaneda, J. Am. Chem. Soc. 2002, 124,
11572; b) M. L. Kantam, K. B. S. Kumar, P. Srinivas, B.
Sreedhar, Adv. Synth. Catal. 2007, 349, 1141; c) A.
Cwik, Z. Hell, F. Figueras, Adv. Synth. Catal. 2006, 348,
523.
[6] M. J. Schultz, C. C. Park, M. S. Sigman, Chem.
Commun. 2002, 3034.
[16] For mechanistic investigations on various types of Pd-
catalyzed aerobic alcohol oxidation, see: a) B. A.
Steinhoff, S. R. Fix, S. S. Stahl, J. Am. Chem. Soc. 2002,
124, 766; b) J. A. Mueller, D. R. Jensen, M. S. Sigman,
J. Am. Chem. Soc. 2002, 124, 8202; c) J. Brink,
I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal.
2002, 344, 355; d) J. Brink, I. W. C. E. Arends, M. Hoo-
genraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal.
2003, 345, 497; e) J. A. Mueller, M. S. Sigman, J. Am.
Chem. Soc. 2003, 125, 7005; f) R. M. Trend, B. M.
[7] a) H. Yang, X. Han, Z. Ma, R. Wang, J. Liu, X. Ji,
Green Chem. 2010, 12, 441; b) T. Hara, M. Ishikawa, J.
Sawada, N. Ichikuni, S. Shimazu, Green Chem. 2009,
11, 2034; c) B. Karimi, A. Zamani, S. Abedi, J. H.
Clark, Green Chem. 2009, 11, 109; d) S. F. J. Hackett,
R. M. Brydson, M. H. Gass, I. Harvey, A. D. Newman
K. Wilson, A. F. Lee, Angew. Chem. 2007, 119, 8747;
Angew. Chem. Int. Ed. 2007, 46, 8593; e) D. Choudhary,
S. Paul, R. Gupta, J. H. Clark, Green Chem. 2006, 8,
Adv. Synth. Catal. 2011, 353, 606 – 616
ꢁ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
615