Carbon-carbon bond formation by ligand-free cross-coupling reaction using palladium catalyst supported on synthetic adsorbent

ChemCatChem

Volumn 4, Issue 4, 2012, Pages 546-558

  Monguchi, Yasunari ^a   Sakai, Keita ^a   Endo, Koichi ^a   Fujita, Yuki ^a   Niimura, Masaru ^b   Yoshimura, Masatoshi ^b   Mizusaki, Tomoteru ^b   Sawama, Yoshinari ^a   Sajiki, Hironao ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b NE Chemcat Corporation   (Japan)

Author keywords

Cross coupling; Heterogeneous catalysis; Mizoroki Heck reaction; Palladium; Suzuki Miyaura reaction

Indexed keywords

ARYL HALIDES; CARBON-CARBON BOND FORMATION; CROSS COUPLING REACTIONS; CROSS-COUPLINGS; INDUSTRIAL PRODUCT; LIGAND-FREE; MIZOROKI-HECK REACTION; NATURAL PRODUCTS; ORGANOBORONIC ACIDS; PALLADIUM CATALYST; SONOGASHIRA REACTIONS; SUZUKI-MIYAURA REACTION; SYNTHETIC ADSORBENTS;

ACETYLENE; CATALYSIS; CATALYSTS; CHARCOAL; OLEFINS; PALLADIUM;

CHEMICAL REACTIONS;

EID: 84859112331     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100345     Document Type: Article

References (127)

1. Metal-Catalyzed Cross-Coupling Reactions 2nded., Vols.1 and 2 (Eds.: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
2. E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823;
3. E. Negishi, T. Takahashi, A. O. King, Org. Synth. Coll. 1993, 8, 430-435.
4. N. Miyaura, K. Yamada, A. Suzuki, Tetrahedron Lett. 1979, 20, 3437-3440;
5. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
6. T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581;
7. R. F. Heck, J. P. Nolley, J. Org. Chem. 1972, 37, 2320-2322;
8. for a review: I. P. Beletstskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066.
9. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173;
10. M. J. Climent, A. Corma, S. Iborra, Chem. Rev. 2011, 111, 1072-1133.
11. C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275-3300;
12. S. Ikegami, H. Hamamoto, Chem. Rev. 2009, 109, 583-593;
13. S.-B. Jang, Tetrahedron Lett. 1997, 38, 1793-1796;
14. M. Terasawa, K. Kaneda, T. Imanaka, S. Teranish, J. Organomet. Chem. 1978, 162, 403-414;
15. K. Inada, N. Miyaura, Tetrahedron 2000, 56, 8661-8664;
16. A. N. Cammidge, N. J. Baines, R. K. Bellingham, Chem. Commun. 2001, 2588-2589;
17. C. A. Parrish, S. L. Buchwald, J. Org. Chem. 2001, 66, 3820-3827;
18. R. Akiyama, S. Kobayashi, Angew. Chem. 2001, 113, 3577-3579; Angew. Chem. Int. Ed. 2001, 40, 3469-3471;
19. M. R. Buchmeiser, T. Schareina, R. Kempe, K. Wurst, J. Organomet. Chem. 2001, 634, 39-46;
20. R. S. Gordon, A. B. Holmes, Chem. Commun. 2002, 640-641;
21. T. Kimura, Y. Uozumi, Synlett 2002, 2045-2048;
22. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Tetrahedron Lett. 2003, 44, 2379-2382;
23. Y. M. A. Yamada, K. Takeda, H. Takahashi, S, Ikegami, J. Org. Chem. 2003, 68, 7733-7741;
24. K. Okamoto, R. Akiyama, S. Kobayashi, Org. Lett. 2004, 6, 1987-1990;
25. K. Okamoto, R. Akiyama, H. Yoshida, T. Yoshida, S. Kobayashi, J. Am. Chem. Soc. 2005, 127, 2125-2135;
26. A. Corma, H. Garcia, A. Leyva, J. Mol. Catal. A 2005, 230, 97-105;
27. Y. Uozumi, M. Kikuchi, Synlett 2005, 1775-1778;
28. A. Desforges, R. Backov, H. Deleuze, O. Mondain-Monval, Adv. Funct. Mater. 2005, 15, 1689-1695;
29. H. Hagio, M. Sugiura, S. Kobayashi, Org. Lett. 2006, 8, 375-378;
30. H. S. He, J. J. Yan, R. Shen, S. Zhuo, P. H. Toy, Synlett 2006, 563-566;
31. S. Schweizer, J.-M. Becht, C. L. Drian, Org. Lett. 2007, 9, 3777-3780;
32. S. Ogasawara, S. Kato, J. Am. Chem. Soc. 2010, 132, 4608-4613;
33. P. Das, D. Sharma, A. K. Shil, A. Kumari, Tetrahedron Lett. 2011, 52, 1176-1178.
34. C. Luo, Y. Zhang, Y. Wang, J. Mol. Catal. A 2005, 229, 7-12.
35. C. P. Mehnert, J. Y. Ying, Chem. Commun. 1997, 2215-2216;
36. C. P. Mehnert, D. W. Weaver, J. Y. Ying, J. Am. Chem. Soc. 1998, 120, 12289-12296;
37. E. B. Mubofu, J. H. Clark, D. J. Macquarrie, Green Chem. 2001, 3, 23-25;
38. S. Paul, J. H. Clark, Green Chem. 2003, 5, 635-638;
39. R. Chanthateyanonth, H. Alper, J. Mol. Catal. A 2003, 201, 23-31;
40. C. Baleizao, A. Corma, H. Garcia, A. Leyva, Chem. Commun. 2003, 606-607;
41. J. Horniakova, T. Raja, Y. Kubota, Y. Sugi, J. Mol. Catal. A 2004, 217, 73-80;
42. K. Simizu, S. Koizumi, T. Hatamachi, H. Yoshida, S. Komai, T. Kodama, Y. Kitayama, J. Catal. 2004, 228, 141-151;
43. L. Li, J.-l. Yan, Chem. Commun. 2004, 1990-1991;
44. C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 2005, 127, 10045-10050;
45. Q. Yang, S. Ma, J. Li, F. Wiao, H. Xiong, Chem. Commun. 2006, 2495-2497;
46. M. Cai, Q. Xu, Y. Huang, J. Mol. Catal. A 2007, 271, 93-97;
47. J. D. Webb, S. MacQuarrie, K. McEleney, C. M. Crudden, J. Catal. 2007, 252, 97-109;
48. G. Budroni, A. Corma, H. Garía, A. Primo, J. Catal. 2007, 251, 345-353.
49. L. Djakovitch, K. Köhler, J. Am. Chem. Soc. 2001, 123, 5990-5999;
50. A. Corma, H. Garcia, A. Leyva, A. Primo, Appl. Catal. A 2003, 247, 41-49;
51. H. Bulut, L. Artok, S. Yilmazu, Tetrahedron Lett. 2003, 44, 289-291;
52. L. Artok, H. Bulut, Tetrahedron Lett. 2004, 45, 3881-3884;
53. G. Durgun, Ö. Aksin, L. Artok, J. Mol. Catal. A 2007, 278, 189-199;
54. B. Yuan, Y. Pan, Y. Li, B. Yin, H. Jiang, Angew. Chem. 2010, 122, 4148-4152; Angew. Chem. Int. Ed. 2010, 49, 4054-4058.
55. K. Kaneda, M. Higuchi, T. Imanaka, J. Mol. Catal. 1990, 63, L33L36;
56. M. Wagner, K. Köhler, L. Djakovitch, S. Weinkauf, V. Hagen, M. Muhler, Top. Catal. 2000, 13, 319-326;
57. B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2002, 124, 14127-14136;
58. M. L. Kantam, S. Roy, M. Roy, M. S. Subhas, P. R. Likhar, B. Sreedhar, B. M. Choudary, Synlett 2006, 2747-2750;
59. D. Kubo, Y. Masui, M. Onaka, Chem. Lett. 2007, 36, 918-919.
60. K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124, 11572-11573;
61. K. Shimizu, T. Kan-no, T. Kodama, H. Hagiwara, Y. Kitayama, Tetrahedron Lett. 2002, 43, 5653-5655;
62. Y. Wan, H. Wang, Q. Zhao, M. Klingstedt, O. Terasaki, D. Zhao, J. Am. Chem. Soc. 2009, 131, 4541-4550;
63. G. M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth, R. Mülhaupt, J. Am. Chem. Soc. 2009, 131, 8262-8270;
64. P.-P. Zhang, X.-X. Zhang, H.-X. Sun, R.-H. Liu, B. Wang, Y.-H. Lin, Tetrahedron Lett. 2009, 50, 4455-4458;
65. M.-J. Jin, D.-H. Lee, Angew. Chem. 2010, 122, 1137-1140; Angew. Chem. Int. Ed. 2010, 49, 1119-1122;
66. S. Wu, H. Ma, X. JIa, Y. Zhong, Z. Lei, Tetrahedron 2011, 67, 250-256.
67. Rotello etal. reported that palladium nanoparticles, which were prepared by the self-assembly of an amine polymer, silica coloid, and palladium clusters and subsequent calcination, catalyzed the hydrogenation of mono-substituted alkene and Mizoroki-Heck reaction: T. H. Galow, U. Drechsler, J. A. Hanson, V. M. Rotello, Chem. Commun. 2002, 1076-1077;
68. Chaudhari etal. developed palladium nanoparticles supported on the amine functionalized zeolite, which catalyzed the hydrogenation of alkenes and alkynes under pressurized hydrogen and the Mizoroki-Heck reaction: S. Mandal, D. Roy, R. V. Chaudhari, M. Sastry, Chem. Mater. 2004, 16, 3714-3724;
69. Fan etal. also prepared phosphine dendrimer-stabilized palladium nanoparticles which could be used for the Suzuki-Miyaura reaction and hydrogenation under pressurized hydrogen: L. Wu, B.-L. Li, Y.-Y. Huang, H.-F. Zhou, Y.-M. He, Q.-H. Fan, Org. Lett. 2006, 8, 3605-3608.
70. S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001.
71. M. Seki, J. Synth. Org. Chem. Jpn. 2006, 64, 853-866;
72. M. Seki, Synthesis 2006, 2975-2992;
73. F.-X. Felpin, T. Ayad, S. Mitra, Eur. J. Org. Chem. 2006, 2679-2690;
74. G. Marck, A. Villiger, R. Buchecker, Tetrahedron Lett. 1994, 35, 3277-3280;
75. D. Gala, A. Stamford, M. Kugelman, Org. Process Res. Dev. 1997, 1, 163-164;
76. D. S. Ennis, J. McManus, W. Wood-Kaczmar, J. Richardson, G. E. Smith, A. Carstairs, Org. Process Res. Dev. 1999, 3, 248-252;
77. C. R. LeBlond, F. Zhao, B. M. Bhanage, M. Shirai, M. Arai, Chem. Eur. J. 2000, 6, 843-848;
78. K. Köhler, R. G. Heidenreich, J. G. E. Krauter, J. Pietsch, Chem. Eur. J. 2002, 8, 622-631;
79. R. G. Heidenreich, K. Köhler, J. G. E. Krauter, J. Pietsch, Synlett 2002, 7, 1118-1122;
80. A. T. Andrews, Y. Sun, J. R. Sowa, Jr., Org. Lett. 2001, 3, 1555-1557;
81. Z. Novák, A. Szabó, J. Répási, A. Kotschy, J. Org. Chem. 2003, 68, 3327-3329;
82. T. Tagata, M. Nishida, J. Org. Chem. 2003, 68, 9412-9415;
83. A. Arcadi, G. Cerichelli, M. Chiarini, M. Correa, D. Zorzan, Eur. J. Org. Chem. 2003, 4080-4086;
84. M. Lysén, K. Köhler, Synlett 2005, 1671-1674.
85. H. Sajiki, T. Kurita, A. Kozaki, G. Zhang, Y. Kitamura, T. Maegawa, 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];
86. 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. Kitamura, T. Maegawa, K. Hirota, Synthesis 2005, 852];
87. 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;
88. Y. Kitamura, A. Sakurai, T. Udzu, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2007, 63, 10596-10602;
89. Y. Kitamura, S. Sako, T. Udzu, A. Tsutui, T. Maegawa, Y. Monguchi, H. Sajiki, Chem. Commun. 2007, 5069-5071;
90. Y. Kitamura, S. Sako, A. Tsutsui, Y. Monguchi, T. Maegawa, Y. Kitade, H. Sajiki, Adv. Synth. Catal. 2010, 352, 718-730.
91. Y. Yabe, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2010, 66, 8654-8660.
92. H. Sajiki, G. Zhang, Y. Kitamura, T. Maegawa, K. Hirota, Synlett 2005, 619-622 [Erratum: H. Sajiki, G. Zhang, Y. Kitamura, T. Maegawa, K. Hirota, Synlett 2005, 1046];
93. S. Mori, T. Yanase, S. Aoyagi, Y. Monguchi, T. Maegawa, H. Sajiki, Chem. Eur. J. 2008, 14, 6994-6999.
94. T. Yanase, S. Mori, Y. Monguchi, H. Sajiki, Chem. Lett. 2011, 40, 910-912.
95. Y. Monguchi, K. Kitamoto, T. Ikawa, T. Maegawa, H. Sajiki, Adv. Synth. Catal. 2008, 350, 2767-2777.
96. T. Adachi, S. Ando, J. Watanabe, J. Chromatogr. A 2002, 944, 41-59;
97. Home page for DIAION HP20 of Mitsubishi Chemical Co., see
98. Y. Monguchi, Y. Fujita, K. Endo, S. Takao, M. Yoshimura, Y. Takagi, T. Maegawa, H. Sajiki, Chem. Eur. J. 2009, 15, 834-837.
99. Boronic Acids (Ed.: D.G. Hall), Wiley-VCH, Weinheim, 2005.
100. M. Feuerstein, H. Doucet, M. Santelli, J. Organomet. Chem. 2003, 687, 327-336;
101. O. Navarro, N. Marion, J. Mei. S. P. Nolan, Chem. Eur. J. 2006, 12, 5142-5148;
102. S. Shi, Y. Zhang, Green Chem. 2008, 10, 868-872.
103. 0, although chloroarenes are desired substrates because of better availability and less production of halogenated wastes by weight, compared with aryl bromides and iodides. See the following paper for the atom economical advantage of aryl chlorides: S. Mukhopadhyay, G. Rothenberg, G. Lando, K. Agbaria, M. Kazanci, Y. Sasson, Adv. Synth. Catal. 2001, 343, 455-459.
104. T. Jeffery, Tetrahedron 1996, 52, 10113-10130.
105. P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767; Angew. Chem. Int. Ed. 2000, 39, 2632-2657.
106. M. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403-6406;
107. D. Mery, K. Heuze, D. Astruc, Chem. Commun. 2003, 1934-1935.
108. D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175-6178; Angew. Chem. Int. Ed. 2003, 42, 5993-5996;
109. A. Arques, D. Aunon, P. Molina, Tetrahedron Lett. 2004, 45, 4337-4340;
110. J. Cheng, Y. Sun, F. Wang, M. Guo, J. Xu, Y. Pan, Z. Zhang, J. Org. Chem. 2004, 69, 5428-5432;
111. S.-B. Park, H. Alper, Chem. Commun. 2004, 1306-1307;
112. M. Feuerstein, H. Doucet, M. Santelli, Tetrahedron Lett. 2005, 46, 1717-1720;
113. T. Mino, Y. Shirae, T. Saito, M. Sakamoto, T. Fujita, J. Org. Chem. 2006, 71, 9499-9502.
114. L. Joucla, G. Cusati, C. Pinel, L. Djakovitch, Appl. Catal. A 2009, 360, 145-153.
115. For the catalytic activity of leached palladium species of heterogeneous catalysts:
116. D. E. Bergbreiter, B. Chen, D. Weatherford, J. Mol. Catal. 1992, 74, 409-419;
117. S. Jayasree, A. Seayad, R. V. Chaudhari, Chem. Commun. 1999, 1067-1068;
118. A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem. 2001, 1131-1133;
119. I. W. Davies, L. Matty, D. L. Hughes, P. J. Reider, J. Am. Chem. Soc. 2001, 123, 10139-10140;
120. D. A. Conlon, B. Pipik, S. Ferdinand, C. R. LeBlond, J. R. Sowa, Jr., B. Izzo, P. Collins, G.-J. Ho, J. M. Williams, Y.-J. Shi, Y. Sun, Adv. Synth. Catal. 2003, 345, 931-935;
121. M. B. Thathagar, J. E. tenElshof, G. Rothenberg, Angew. Chem. 2006, 118, 2952-2956; Angew. Chem. Int. Ed. 2006, 45, 2886-2890;
122. A. V. Gaikwad, A. Holuigue, M. B. Thathagar, J. E. tenElshof, G. Rothenberg, Chem. Eur. J. 2007, 13, 6908-6913;
123. L. D. Pachón, G. Rothenberg, Appl. Organomet. Chem. 2008, 22, 288-299; also see refs. [14g] and [15e].
124. The palladium particle size on the recovered 10% Pd/HP20 increased to ca. 13nm based on the XRD analysis (≈4nm for the palladium particle size on the fresh 10% Pd/HP20) after the Mizoroki-Heck reaction unlike the case of the 10% Pd/HP20-catalyzed Suzuki-Miyaura reaction.
125. 3N in NMP at 80°C. When Celite was added to the reaction mixture, no precipitates formed and Pd species were absorbed on Celite. The resulting Pd on Celite could be reused until at least three runs for the Mizoroki-Heck reaction after the activation using iodine or bromine. A. H. M. deVries, F. J. Parlevliet, L. S. deVondervoort, J. H. M. Mommers, H. J. W. Henderickx, M. A. M. Walet, J. G. deVries, Adv. Synth. Catal. 2002, 344, 996-1002; also see ref.[30h].
126. Rothenberg etal. proved that Pd species were leached into the reaction media during the Pd nanoclusters-catalyzed Mizoroki-Heck and Suzuki-Miyaura reactions, and they were found to work as actual active species by the experiments using a special two-component membrane reactor consisting of two stainless steel compartments separated by a 5nm alumina membrane filter, see ref.[30f-h]].
127. When 10% Pd/C was used for the cross-coupling reaction between 4'-iodoacetophenone and 3-butyn-1-ol in 50% iPrOH at 80°C, approximately 25% of Pd metal was found to leach from 10% Pd/C, see ref.[17b].