Palladium oxidase catalysis: Selective oxidation of organic chemicals by direct dioxygen-coupled turnover

Angewandte Chemie - International Edition

Volumn 43, Issue 26, 2004, Pages 3400-3420

  Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Homogeneous catalysis; Oxidation; Oxidative coupling; Oxygen; Palladium

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; CATALYSTS; OXIDATION; OXIDES; SUBSTRATES;

DIOXYGEN-COUPLING; PALLADIUM OXIDASE CATALYSIS; SELECTIVE OXIDATION;

PALLADIUM COMPOUNDS;

ALCOHOL; ALKENE DERIVATIVE; BENZOQUINONE; CARBON; COPPER DERIVATIVE; HYDROGEN PEROXIDE; LIGAND; ORGANIC COMPOUND; OXYGEN; PALLADIUM; PYRIDINE; SPARTEINE; SULFONIC ACID DERIVATIVE;

CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMISTRY; CYCLIZATION; DECOMPOSITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

ALCOHOLS; ALKENES; CATALYSIS; HYDROGEN PEROXIDE; ORGANOMETALLIC COMPOUNDS; OXIDANTS; OXIDATION-REDUCTION; OXIDOREDUCTASES; OXYGEN; PALLADIUM;

EID: 4143153074     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300630     Document Type: Review

References (318)

1. K. Weissermel, H.-J. Arpe, Industrial Organic Chemistry, 3rd ed., VCH, New York, 1997.
2. See, for example: a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojiima), Wiley-VCH, New York, 2000, pp. 231-285;
3. b) E. N. Jacobsen in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel, L. S. Hegedus), Pergamon, New York, 1995, pp. 1097-1135;
4. c) T. Katsuki in reference [2a], pp. 287-325;
5. d) R. A. Johnson, K. B. Sharpless in reference [2a], pp. 357-398;
6. e) H. B. Kagan in reference [2a], pp. 327-356.
7. For leading references, see: a) Oxygenases and Model Systems (Ed.: T. Funabiki), Kluwer, Boston, 1997;
8. b) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792;
9. c) R. Neumann, M. Dahan, Nature 1997, 388, 353-355;
10. d) C. Döbler, G. M. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10289-10297.
11. a) J. Smidt, W. Hafner, R. Jira, J. Sedlmeier, R. Sieber, R. Rüttinger, H. Kojer, Angew. Chem. 1959, 71, 176-182;
12. b) R. Jira in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2002, pp. 386-405;
13. c) I. I. Moiseev, M. N. Vargaftik in reference [4b], pp. 406-412.
14. P. M. Henry, Palladium Catalyzed Oxidation of Hydrocarbons, Kluwer, Boston, 1980.
15. J. Tsuji, Palladium Reagents and Catalysts, Wiley, New York, 1995.
16. For leading references, see: a) Metal-catalyzed Cross-coupling Reactions (Eds,: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998;
17. b) Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, Vol. I, II (Eds.: M. Beller, C. Bolm), Wiley-VCH, New York, 1998;
18. c) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-31366.
19. a) J.-E. Bäckvall, Acc. Chem. Res. 1983, 16, 335-342;
20. b) J. Tsuji, Synthesis 1984, 369-384;
21. c) T. Hosokawa, S.-I. Murahashi, Acc. Chem. Res. 1990, 23, 49-54;
22. d) J. Tsuji in Comprehensive Organic Synthesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, pp. 449-468;
23. e) A. Heumann, K.J. Jens, M. Réglier, Prog. Inorg. Chem. 1994, 42, 483-576;
24. f) J. M. Takacs, X.-t. Jiang, Curr. Org. Chem. 2003, 7, 369-396;
25. g) J. Muzart, Tetrahedron 2003, 59, 5789-5816.
26. For leading references on colloidal and heterogeneous palladium-catalyzed oxidations, see: a) M. N. Vargaftik, V. P. Zagorodnikov, I. P. Stolarov, I. I. Moiseev, D. I. Kochubey, V. A. Likholobov, A. L. Chuvilin, K. I. Zamaraev, J. Mol. Catal. 1989, 53, 315-348;
27. b) K. Kaneda, M. Fujii, K. Morioka, J. Org. Chem. 1996, 61, 4502-4503;
28. c) K. Kaneda, Y. Fujie, K. Ebitani, Tetrahedron Lett. 1997, 38, 9023-9026;
29. d) K. Ebitani, Y. Fujie, K. Kaneda, Langmuir 1999, 15, 3557-3562;
30. e) T. Nishimura, N. Kakiuchi, M. Inoue, S. Uemura, Chem. Commun. 2000, 1245-1246;
31. f) N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620-6625;
32. g) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2002, 124, 11572-11573;
33. h) G. Kovtun, T. Kameneva, S. Hladyi, M. Starchevsky, Y. Pazdersky, I. Stolarov, M. Vargaftik, I. Moiseev, Adv. Synth. Catal. 2002, 344, 957-964;
34. i) K.-M. Choi, T. Akita, T. Mizugaki, K. Ebitani, K. Kaneda, New J. Chem. 2003, 27, 324-328;
35. j) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197.
36. j) Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207; Angew. Chem. Int. Ed. 2003, 42, 194-197.
37. a) I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119-1122;
38. b) R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518-5526.
39. a) J. M. Davidson, C. Triggs, Chem. Ind. 1967, 1361;
40. b) M. O. Unger, R. A. Fouty, J. Org. Chem. 1969, 34, 18-21;
41. c) H. Itatani, H. Yoshimoto, Chem. Ind. 1971, 674-675.
42. G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62; Angew. Chem. Int. Ed. Engl. 1967, 6, 92-93.
43. G. Wilke, H. Schott, P. Heimbach, Angew. Chem. 1967, 79, 62; Angew. Chem. Int. Ed. Engl. 1967, 6, 92-93.
44. a) J. S. Valentine, Chem. Rev. 1973, 73, 235-245;
45. b) T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1977, 99, 2134-2140;
46. c) S. Otsuka, A. Nakamura, Y. Tatsuno, M. Miki, J. Am. Chem. Soc. 1972, 94, 3761-3767;
47. d) S. Otsuka, A. Nakamura, Y. Tatsuno, J. Am. Chem. Soc. 1969, 91, 6994-6999;
48. e) T. Yoshida, K. Tatsumi, M. Matsumoto, K. Nakatsu, A. Nakamura, T. Fueno, S. Otsuka, Nouv. J. Chim. 1979, 3, 761-774.
49. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
50. S. S. Stahl, J. L. Thorman, R. C. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188-7189.
51. a) R. van Asselt, C. J. Elsevier, W. J. J. Smeets, A. L. Spek, Inorg. Chem. 1994, 33, 1521-1531;
52. b) S. M. Reid, J. T. Mague, M. J. Fink, J. Organomet. Chem. 2000, 616, 10-18;
53. c) S. S. Stahl, J. L. Thorman, N. de Silva, I. A. Guzei, R. W. Clark, J. Am. Chem. Soc. 2003, 125, 12-13.
54. a) M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673;
55. b) C. Amatore, A. Jutand, Coord. Chem. Rev. 1998, 178-180, 511-528;
56. c) L. M. Alcazar-Roman, J. F. Hartwig, A. L. Rheingold, L. M. Liable-Sands, I. A. Guzei, J. Am. Chem. Soc. 2000, 122, 4618-4630;
57. d) A. K. de K. Lewis, S. Caddick, F. G. N. Cloke, N. C. Billingham, P. B. Hitchcock, J. Leonard, J. Am. Chem. Soc. 2003, 125, 10066-10073.
58. For other studies of peroxopalladium(II) protonolysis, see: a) S. Muto, H. Ogata, Y. Kamiya, Chem. Lett. 1975, 809-812;
59. b) S. Muto, Y. Kamiya, Bull. Chem. Soc. Jpn. 1976, 49, 2587-2589;
60. c) S. Muto, K. Tasaka, Y. Kamiya, Bull. Chem. Soc. Jpn. 1977, 50, 2493-2494.
61. a) D. A. Bianchi, R. N. Bortolo, R. N. D'Aloisio, M. N. Ricci, S. C. Soattini (Enichem S.p.A.), EP0-808-796A1, 1997;
62. b) D. Bianchi, R. Bortolo, R. D'Aloisio, M. Ricci, Angew. Chem. 1999, 111, 734-736; Angew. Chem. Int. Ed. 1999, 38, 706-708;
63. b) D. Bianchi, R. Bortolo, R. D'Aloisio, M. Ricci, Angew. Chem. 1999, 111, 734-736; Angew. Chem. Int. Ed. 1999, 38, 706-708;
64. c) D. Bianchi, R. Bortolo, R. D'Aloisio, M. Ricci, J. Mol. Catal. A 1999, 150, 87-94;
65. d) D. Bianchi, R. Bortolo, R. D'Aloisio, C. Querci, M. Ricci, Stud. Surf. Sci. Catal. 1999, 126, 481-484;
66. e) R. Bortolo, D. Bianchi, R. D'Aloisio, C. Querci, M. Ricci, J. Mol. Catal. A 2000, 153, 25-29.
67. W.R. Thiel, Angew. Chem. 1999, 111, 3349-3351; Angew. Chem. Int. Ed. 1999, 38, 3157-3158.
68. W.R. Thiel, Angew. Chem. 1999, 111, 3349-3351; Angew. Chem. Int. Ed. 1999, 38, 3157-3158.
69. a) K. D. Karlin, S. Kaderli, A. D. Zuberbühler, Acc. Chem. Res. 1997, 30, 139-147;
70. b) W. B. Tolman, Acc. Chem. Res. 1997, 30, 227-237;
71. c) V. Mahadevan, R. J. M. K. Gebbink, T. D. P. Stack, Curr. Opin. Chem. Biol. 2000, 4, 228-234;
72. d) E. I. Solomon, P. Chen, M. Metz, S.-K. Lee, A. E. Palmer, Angew. Chem. 2001, 113, 4702-4724; Angew. Chem. Int. Ed. 2001, 40, 4570-4590.
73. d) E. I. Solomon, P. Chen, M. Metz, S.-K. Lee, A. E. Palmer, Angew. Chem. 2001, 113, 4702-4724; Angew. Chem. Int. Ed. 2001, 40, 4570-4590.
74. a) G.-J. ten Brink, I. W. C. E. Arends, G. Papadogianakis, R. A. Sheldon, Chem. Commun. 1998, 2359-2360;
75. b) G.-J. ten Brink, I. W. C. E. Arends, G. Papadogianakis, R. A. Sheldon, Appl. Catal. A 2000, 194-195, 435-442.
76. a) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636-1639;
77. b) R. A. Sheldon, I. W. C. E. Arends, G.-J. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774-781;
78. c) G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355-369;
79. d) G.-J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal. 2003, 345, 497-505.
80. a) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, Tetrahedron Lett. 1998, 39, 6011-6014;
81. b) T. Nishimura, T. Onoue, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 6750-6755;
82. c) T. Nishimura, Y. Maeda, N. Kakiuchi, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 4301-4305.
83. a) J. H. Bayston, R. N. Beale, N. K. King, M. E. Winfield, Aust. J. Chem. 1963, 16, 954-968;
84. b) J. H. Bayston, M. E. Winfield, J. Catal. 1964, 3, 123-128;
85. c) H. L. Roberts, W. R. Symes, J. Chem. Soc. A 1968, 1450-1453;
86. d) L. E. Johnston, J. A. Page, Can. J. Chem. 1969, 47, 4241-4246;
87. e) R. D. Gillard, B. T. Heaton, D. H. Vaughan, J. Chem. Soc. A 1970, 3126-3130;
88. f) J. F. Endicott, C.-L. Wong, T. Inoue, P. Natarajan, Inorg. Chem. 1979, 18, 450-454;
89. g) M. T. Atlay, M. Preece, G. Strukul, B. R. James, Can. J. Chem. 1983, 61, 1332-1338;
90. h) D. D. Wick, K. I. Goldberg, J. Am. Chem. Soc. 1999, 121, 11900-11901.
91. a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, C. J. Urch in Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, Vol. II (Eds.: M. Beller, C. Bolm), Wiley-VCH, New York, 1998, pp. 350-360;
92. b) R. A. Sheldon, I. W. C. E. Arends, A. Dijksman, Catal. Today 2000, 57, 157-166.
93. J. J. Berzelius, Ann. Phys. Chem. 1828, 13, 435-488.
94. W. G. Lloyd, J. Org. Chem. 1967, 32, 2816-2819.
95. T. F. Blackburn, J. Schwartz, J. Chem. Soc. Chem. Commun. 1977, 157-158; Correction: T. F. Blackburn, J. Schwartz, J. Chem. Soc. Chem. Commun. 1978, 632.
96. T. F. Blackburn, J. Schwartz, J. Chem. Soc. Chem. Commun. 1977, 157-158; Correction: T. F. Blackburn, J. Schwartz, J. Chem. Soc. Chem. Commun. 1978, 632.
97. E. Gómez-Bengoa, P. Noheda, A. M. Echavarren, Tetrahedron Lett. 1994, 35, 7097-7098.
98. S. Ail-Mohand, F. Hénin, J. Muzart, Tetrahedron Lett. 1995, 36, 2473-2476.
99. K. P. Peterson, R. C. Larock, J. Org. Chem. 1998, 63, 3185-3189.
100. a) R. C. Larock, T. R. Hightower, J. Org. Chem. 1993, 58, 5298-5300;
101. b) R. C. Larock, T. R. Hightower, L. A. Hasvold, K. P. Peterson, J. Org. Chem. 1996, 61, 3584-3585;
102. c) R. C. Larock, L. Wei, T. R. Hightower, Synlett 1998, 522-524.
103. R. C. Larock, T. R. Hightower, G. A. Kraus, P. Hahn, D. Zheng, Tetrahedron Lett. 1995, 36, 2423-2426.
104. a) R. A. T. M. van Benthem, H. Hiemstra, J. J. Michels, W. N. Speckamp, J. Chem. Soc. Chem. Commun. 1994, 357-359;
105. b) R. A. T. M. van Benthem, H. Hiemstra, G. R. Longarela, W. N. Speckamp, Tetrahedron Lett. 1994, 35, 9281-9284;
106. c) R. A. T. M. van Benthem, H. Hiemstra, P. W. N. M. van-Leeuwen, J. W. Geus, W. N. Speckamp, Angew. Chem. 1995, 107, 500-503; Angew. Chem. Int. Ed. Engl. 1995, 34, 457-460.
107. c) R. A. T. M. van Benthem, H. Hiemstra, P. W. N. M. van-Leeuwen, J. W. Geus, W. N. Speckamp, Angew. Chem. 1995, 107, 500-503; Angew. Chem. Int. Ed. Engl. 1995, 34, 457-460.
108. a) M. Rönn, J.-E. Bäckvall, P. G. Andersson, Tetrahedron Lett. 1995, 36, 7749-7752;
109. b) M. Rönn, P. G. Andersson, J.-E. Bäckvall, Acta Chem. Scand. 1997, 51, 773-777;
110. c) M. Rönn, P. G. Andersson, J.-E. Bäckvall, Tetrahedron Lett. 1997, 38, 3603-3606.
111. a) M. Toyota, T. Wada, K. Fukumoto, M. Ihara, J. Am. Chem. Soc. 1998, 120, 4916-4925;
112. b) M. Toyota, M. Rudyanto, M. Ihara, Tetrahedron Lett. 2000, 41, 8929-8932;
113. c) M. Toyota, T. Odashima, T. Wada, M. Ihara, J. Am. Chem. Soc. 2000, 122, 9036-9037;
114. d) M. Toyota, T. Wada, M. Ihara, J. Org. Chem. 2000, 65, 4565-4570;
115. e) M. Toyota, A. Ilangovan, R. Okamoto, T. Masaki, M. Arakawa, M. Ihara, Org. Lett. 2002, 4, 4293-4296;
116. f) M. Toyota, M. Ihara, Synlett 2002, 1211-1222;
117. g) M. Toyota, M. Rudyanto, M. Ihara, J. Org. Chem. 2002, 67, 3374-3386;
118. h) M. Toyota, M. Sasaki, M. Ihara, Org. Lett. 2003, 5, 1193-1195.
119. B. A. Steinhoff, S. R. Fix, S. S. Stahl, J. Am. Chem. Soc. 2002, 124, 766-767.
120. a) B. B. Wayland, R. F. Schramm, Inorg. Chem. 1969, 8, 971-976;
121. b) D. P. Bancroft, F. A. Cotton, M. Verbruggen, Acta Crystallogr. Sect. C 1989, 45, 1289-1292;
122. c) A. I. Stash, T. I. Perepelkova, S. V. Kravtsova, Y. G. Noskov, I. P. Romm, Russ. J. Coord. Chem. 1998, 24, 36-39.
123. This proposal is not consistent with observations in our own laboratory, which suggest that hydrogen peroxide disproportionation is slower in the presence of molecular sieves: B. A. Steinhoff, S. S. Stahl, unpublished results.
124. S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172-174; Angew. Chem. Int. Ed. 2002, 41, 164-166.
125. S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172-174; Angew. Chem. Int. Ed. 2002, 41, 164-166.
126. B. A. Steinhoff, S. S. Stahl, Org. Lett. 2002, 4, 4179-4181.
127. a) C. Amatore, A. Jutand, J. Organomet. Chem. 1999, 576, 254-278;
128. b) C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc. 1993, 115, 9531-9541;
129. c) L. M. Alcazar-Roman, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 12905-12906.
130. a) A. El-Qisairi, O. Hamed, P. M. Henry, J. Org. Chem. 1998, 63, 2790-2791;
131. b) O. Hamed, P. M. Henry, Organometallics 1998, 17, 5184-5189;
132. c) A. El-Qisairi, P. M. Henry, J. Organomet. Chem. 2000, 603, 50-60;
133. d) A. K. El-Qisairi, H.A. Qaseer, P. M. Henry, J. Organomet. Chem. 2002, 656, 168-176;
134. e) A. K. El-Qisairi, H. A. Qaseer, G. Katsigras, P. Lorenzi, U. Trivedi, S. Tracz, A. Hartman, J. A. Miller, P. M. Henry, Org. Lett. 2003, 5, 439-441.
135. a) T. Hosokawa, S. Miyagi, S.-I. Murahashi, A. Sonoda, J. Org. Chem. 1978, 43, 2752-2757;
136. b) T. Hosokawa, T. Uno, S. Inui, S.-I. Murahashi, J. Am. Chem. Soc. 1981, 103, 2318-2323;
137. c) T. Hosokawa, Y. Imada, S. I. Murahashi, Bull. Chem. Soc. Jpn. 1985, 58, 3282-3290;
138. d) T. Hosokawa, C. Okuda, S.-I. Murahashi, J. Org. Chem. 1985, 50, 1282-1287;
139. ) T. Hosokawa, T. Kono, T. Shinohara, S.-I. Murahashi, J. Organomet. Chem. 1989, 370, C13-C16.
140. a) A. Thorarensen, A. Palmgren, K. Itami, J.-E. Bäckvall, Tetrahedron Lett. 1997, 38, 8541-8544;
141. b) K. Itami, A. Palmgren, A. Thorarensen, J.-E. Bäckvall, J. Org. Chem. 1998, 63, 6466-6471;
142. c) H. K. Cotton, R. C. Verboom, L. Johansson, B. J. Plietker, J.-E. Bäckvall, Organometallics 2002, 21, 3367-3375.
143. a) Y. Uozumi, K. Kato, T. Hayashi, J. Am. Chem. Soc. 1997, 119, 5063-5064;
144. b) Y. Uozumi, K. Kato, T. Hayashi, J. Org. Chem. 1998, 63, 5071-5075;
145. c) Y. Uozumi, H. Kyota, K. Kato, M. Ogasawara, T. Hayashi, J. Org. Chem. 1999, 64, 1620-1625.
146. M. A. Arai, M. Kuraishi, T. Arai, H. Sasai, J. Am. Chem. Soc. 2001, 123, 2907-2908.
147. a) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2001, 123, 7725-7726;
148. b) J. T. Bagdanoff, E. M. Ferreira, B. M. Stoltz, Org. Lett. 2003, 5, 835-837;
149. c) R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2003, 115, 2998-3001; Angew. Chem. Int. Ed. 2003, 42, 2892-2895.
150. c) R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2003, 115, 2998-3001; Angew. Chem. Int. Ed. 2003, 42, 2892-2895.
151. a) D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Am. Chem. Soc. 2001, 123, 7475-7476;
152. b) J. A. Mueller, D. R. Jensen, M. S. Sigman, J. Am. Chem. Soc. 2002, 124, 8202-8203;
153. c) D. R. Jensen, M. S. Sigman, Org. Lett. 2003, 5, 63-65;
154. d) S. K. Mandal, D. R. Jensen, J. S. Pugsley, M. S. Sigman, J. Org. Chem. 2003, 68, 4600-4603;
155. e) J. A. Mueller, M. S. Sigman, J. Am. Chem. Soc. 2003, 125, 7005-7013;
156. f) S.K. Mandal, M. S. Sigman, J. Org. Chem. 2003, 68, 7535-7537.
157. M. J. Dearden, C. R. Firkin, J.-P. R. Hermet, P. O'Brien, J. Am. Chem. Soc. 2002, 124, 11870-11871.
158. K. Hallman, C. Moberg, Adv. Synth. Catal. 2001, 343, 260-263.
159. a) M. J. Schultz, C. C. Park, M. S. Sigman, Chem. Commun. 2002, 3034-3035;
160. b) D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940-3943; Angew. Chem. Int. Ed. 2003, 42, 3810-3813.
161. b) D. R. Jensen, M. J. Schultz, J. A. Mueller, M. S. Sigman, Angew. Chem. 2003, 115, 3940-3943; Angew. Chem. Int. Ed. 2003, 42, 3810-3813.
162. K. R. Seddon, A. Stark, Green Chem. 2002, 4, 119-123.
163. F. C. Phillips, Am. Chem. J. 1894, 16, 255-277.
164. T. Nishimura, N. Kakiuchi, T. Onoue, K. Ohe, S. Uemura, J. Chem. Soc. Perkin Trans. 1 2000, 1915-1918.
165. a) M. Roussel, H. Mimoun, J. Org. Chem. 1980, 45, 5387-5390;
166. b) H. Mimoun, R. Charpentier, A. Mitschler, J. Fischer, R. Weiss, J. Am. Chem. Soc. 1980, 102, 1047-1054;
167. c) H. Mimoun, Angew. Chem. 1982, 94, 750-766; Angew. Chem. Int. Ed. Engl. 1982, 21, 734-750.
168. c) H. Mimoun, Angew. Chem. 1982, 94, 750-766; Angew. Chem. Int. Ed. Engl. 1982, 21, 734-750.
169. a) T. Hosokawa, T. Ohta, S.-I. Murahashi, J. Chem. Soc. Chem. Commun. 1983, 848-849;
170. b) T. Hosokawa, T. Ohta, S. Kanayama, S.-I. Murahashi, J. Org. Chem. 1987, 52, 1758-1764;
171. c) T. Hosokawa, Y. Ataka, S.-I. Murahashi, Bull. Chem. Soc. Jpn. 1990, 63, 166-169;
172. d) see also: W. G. Lloyd, B. J. Luberoff, J. Org. Chem. 1969, 34, 3949-3952.
173. a) T. Hosokawa, M. Takano, Y. Kuroki, S.-I. Murahashi, Tetrahedron Lett. 1992, 33, 6643-6646;
174. b) See also: F. Ragaini, T. Longo, S. Cenini, J. Mol. Catal. A 1996, 110, L171-L175.
175. V. I. Timokhin, N. R. Anastasi, S. S. Stahl, J. Am. Chem. Soc. 2003, 125, 12996-12997.
176. a) J.-E. Bäckvall, A. K. Awasthi, Z. D. Renko, J. Am. Chem. Soc. 1987, 109, 4750-4752;
177. b) J.-E. Bäckvall, R. B. Hopkins, H. Grennberg, M. M. Mader, A. K. Awasthi, J. Am. Chem. Soc. 1990, 112, 5160-5166;
178. c) H. Grennberg, A. Gogoll, J.-E. Bäckvall, J. Org. Chem. 1991, 56, 5808-5811;
179. d) H. Grennberg, S. Faizon, J.-E. Bäckvall, Angew. Chem. 1993, 105, 269-271; Angew. Chem. Int. Ed. Engl. 1993, 32, 263-264;
180. d) H. Grennberg, S. Faizon, J.-E. Bäckvall, Angew. Chem. 1993, 105, 269-271; Angew. Chem. Int. Ed. Engl. 1993, 32, 263-264;
181. e) K. Bergstad, H. Grennberg, J.-E. Bäckvall, Organometallics 1998, 17, 45-50;
182. f) J. Wöltinger, J.-E. Bäckvall, A. Zsigmond, Chem. Eur. J. 1999, 5, 1460-1467.
183. J. E. Bäckvall, R. B. Hopkins, Tetrahedron Lett. 1988, 29, 2885-2888.
184. A variety of different nucleophiles have been used; see the following for selected early and recent examples: organo-mercury reagents: a) reference [10a];
185. b) R. F. Heck, J. Am. Chem. Soc. 1971, 93, 6896-6901;
186. aryl amines, -phosphanes, -arsanes, -stibanes, and -bismuthane: c) R. Asano, I. Moritani, Y. Fujiwara, S. Teranishi, Bull. Chem. Soc. Jpn. 1973, 46, 2910-2911;
187. d) C. S. Cho, S. Motofusa, K. Ohe, S. Uemura, Bull. Chem. Soc. Jpn. 1996, 69, 2341-2348;
188. alkyl lithium: e) S. Murahashi, M. Yamamura, N. Mita, J. Org. Chem. 1977, 42, 2870-2874.
189. organomagnesium: f) N.-T. Luong-Thi, H. Riviere, J. Chem. Soc. Chem. Commun. 1978, 918-919;
190. aryl stannanes: g) H. Oda, M. Morishita, K. Fugami, H. Sano, M. Kosugi, Chem. Lett. 1996, 811-812;
191. h) K. Fugami, S. Hagiwara, H. Oda, M. Kosugi, Synlett 1998, 477-478;
192. i) K. Hirabayashi, J. Ando, Y. Nishihara, A. Mori, T. Hiyama, Synlett 1999, 99-101;
193. aryl and vinyl boronic acids and esters: j) X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313-3316;
194. aryl and alkenyl silanols: k) K. Hirabayashi, Y. Nishihara, A. Mori, T. Hiyama, Tetrahedron Lett. 1998, 39, 7893-7896;
195. l) K. Hirabayashi, J. Ando, J. Kawashima, Y. Nishihara, A. Mori, T. Hiyama, Bull. Chem. Soc. Jpn. 2000, 73, 1409-1417;
196. m) K. Hirabayashi, T. Kondo, F. Toriyama, Y. Nishihara, A. Mori, Bull. Chem. Soc. Jpn. 2000, 73, 749-750;
197. aryl phosphonic acids: n) A. Inoue, H. Shinokubo, K. Oshima, J. Am. Chem. Soc. 2003, 125, 1484-1485.
198. K. Matoba, S. Motofusa, C. S. Cho, K. Ohe, S. Uemura, J. Organomet. Chem. 1999, 574, 3-10.
199. T. Ohe, T. Tanaka, M. Kuroda, C. S. Cho, K. Ohe, S. Uemura, Bull. Chem. Soc. Jpn. 1999, 72, 1851-1855.
200. J. P. Parrish, Y. C. Jung, S. I. Shin, K. W. Jung, J. Org. Chem. 2002, 67, 7127-7130.
201. Y. C. Jung, R. K. Mishra, C. H. Yoon, K. W. Jung, Org. Lett. 2003, 5, 2231-2234.
202. For reviews most pertinent to the present discussion, see: a) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879-2932;
203. b) S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298-2311; Angew. Chem. Int. Ed. 1998, 37, 2181-2192;
204. b) S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298-2311; Angew. Chem. Int. Ed. 1998, 37, 2181-2192;
205. c) A. Sen, Acc. Chem. Res. 1998, 31, 550-557;
206. d) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639; Correction: C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 844;
207. d) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639; Correction: C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 844;
208. e) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769.
209. For representative examples, see: a) Y. Fujiwara, I. Moritani, M. Matsuda, S. Teranishi, Tetrahedron Lett. 1968, 3863-3865;
210. b) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166-7169;
211. c) O. Maruyama, M. Yoshidomi, Y. Fujiwara, H. Taniguchi, Chem. Lett. 1979, 1229-1230;
212. d) T. Itahara, M. Ikeda, T. Sakakibara, J. Chem. Soc. Perkin Trans. 1 1983, 1361-1363;
213. e) J. Tsuji, H. Nagashima, Tetrahedron 1984, 40, 2699-2702;
214. f) M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. 1997, 1103-1104;
215. g) M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, J. Org. Chem. 1998, 63, 5211-5215;
216. h) K. Mikami, M. Hatano, M. Terada, Chem. Lett. 1999, 55-56;
217. i) C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097-2100;
218. j) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586-1587;
219. k) T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476-1477.
220. a) R. S. Shue, J. Chem. Soc. Chem. Commun. 1971, 1510-1511;
221. b) R. S. Shue, J. Catal. 1972, 26, 112-117;
222. c) R. S. Shue (Phillips Petroleum Co.), US 3,775,511, 1973.
223. M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. 2003, 115, 3636-3639; Angew. Chem. Int. Ed. 2003, 42, 3512-3515.
224. M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. 2003, 115, 3636-3639; Angew. Chem. Int. Ed. 2003, 42, 3512-3515.
225. a) H. Weissman, X. Song, D. Milstein, J. Am. Chem. Soc. 2001, 123, 337-338;
226. b) T. Matsumoto, H. Yoshida, Chem. Lett. 2000, 1064-1065;
227. c) T. Matsumoto, R. A. Periana, D. J. Taube, H. Yoshida, J. Catal. 2002, 206, 272-280.
228. For recent reviews, see: a) N. Petragnani, H. A. Stefani, C. J. Valduga, Tetrahedron 2001, 57, 1411-1448;
229. b) M. Frederickson, R. Grigg, Org. Prep. Proced. Int. 1997, 29, 33-62;
230. c) M. Frederickson, R. Grigg, Org. Prep. Proced. Int. 1997, 29, 63-115.
231. See, for example: a) L. S. Hegedus, J. Mol. Catal. 1983, 19, 201-211;
232. b) L. S. Hegedus, Angew. Chem. 1988, 100, 1147-1161; Angew. Chem. Int. Ed. Engl. 1988, 27, 1113-1126.
233. b) L. S. Hegedus, Angew. Chem. 1988, 100, 1147-1161; Angew. Chem. Int. Ed. Engl. 1988, 27, 1113-1126.
234. Evidence for the formation of mononuclear complexes has been obtained in "heterogeneous" palladium-catalyzed cross-coupling reactions: a) I. W. Davies, L. Matty, D. L. Hughes, P. J. Reider, J. Am. Chem. Soc. 2001, 123, 10139-10140;
235. A. Biffis, M. Zecca, M. Basato, J. Mol. Catal. A 2001, 173, 249-274.
236. E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578-9579.
237. R. van Helden, G. Verberg, Recl. Trav. Chim. Pays-Bas 1965, 84, 1263-1273.
238. a) J. M. Davidson, C. Triggs, Chem. Ind. 1966, 457;
239. b) reference [11a];
240. c) J. M. Davidson, C. Triggs, J. Chem. Soc. A 1968, 1324-1330.
241. a) reference [11 c];
242. b) H. Iataaki, H. Yoshimoto, J. Org. Chem. 1973, 38, 76-79;
243. c) H. Yoshimoto, H. Itatani, Bull. Chem. Soc. Jpn. 1973, 46, 2490-2492;
244. d) H. Yoshimoto, H. Itatani, J. Catal. 1973, 31, 8-12;
245. ) M. Kashima, H. Yoshimoto, H. Itatani, J. Catal. 1973, 29, 92-98.
246. A number of cocatalytic (especially Pd/Cu and Pd/polyoxometallate) methods for the oxidative coupling of arenes have been developed; for leading references, see: a) G. U. Mennenga, A. I. Rudenkov, K. I. Matveev, I. V. Kozhevnikov, React. Kinet. Catal. Lett. 1976, 5, 401-406;
247. b) A. I. Rudenkov, G.U. Mennenga, L. N. Rachkovskaya, K. I. Matveev, I. V. Kozhevnikov, Kinet. Katal. 1977, 18, 915-920;
248. c) V. E. Tarabanko, I. V. Kozhevnikov, K. I. Matveev, React. Kinet. Catal. Lett. 1978, 8, 77-79;
249. d) A. K. Yatsimirsky, S. A. Deiko, A. D. Ryabov, Tetrahedron 1983, 39, 2381-2392;
250. e) S. H. Lee, K.H. Lee, J. S. Lee, J. D. Jung, J. S. Shim, J. Mol. Catal. A 1997, 115, 241-246;
251. f) M. Okamoto, T. Yamaji, Chem. Lett. 2001, 212-213;
252. g) S. Mukhopadhyay, G. Rothenberg, G. Lando, K. Agbaria, M. Kazanci, Y. Sasson, Adv. Synth. Catal. 2001, 343, 455-459;
253. h) T. Yokota, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2002, 344, 849-854;
254. i) M. Okamoto, M. Watanabe, T. Yamaji, J. Organomet. Chem. 2002, 664, 59-65.
255. See also: a) reference [11b];
256. b) Y. Fujiwara, R. Asano, I. Moritani, S. Teranishi, J. Org. Chem. 1976, 41, 1681-1683;
257. c) L. J. Ackerman, J. P. Sadighi, D. M. Kurtz, J. A. Labinger, J. E. Bercaw, Organometallics 2003, 22, 3884-3890.
258. S. Murai in Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, Berlin, 1999, pp. 47-79.
259. a) H. Itatani, A. Shiotani, A. Yokota, (Ube Industries, Ltd., Japan), US 4,292,435, 1981;
260. b) H. Itatani, A. Shiotani, A. Yokota, (Ube Industries, Ltd., Japan), US 4,338,456, 1982;
261. c) A. Shiotani, M. Yoshikiyo, H. Itatani, J. Mol. Catal. 1983, 18, 23-31;
262. d) A. Shiotani, H. Itatani, T. Inagaki, J. Mol. Catal. 1986, 34, 57-66.
263. For leading references, see: a) reference [7a];
264. b) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
265. b) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
266. a) M. Moreno-Mañas, M. Pérez, R. Pleixats, J. Org. Chem. 1996, 61, 2346-2351;
267. b) K. A. Smith, E. M. Campi, W. R. Jackson, S. Marcuccio, C. G. M. Naeslund, G. B. Deacon, Synlett 1997, 131-132;
268. c) M. S. Wong, X. L. Zhang, Tetrahedron Lett. 2001, 42, 4087-4089;
269. d) J. P. Parrish, Y. C. Jung, R. J. Floyd, K. W. Jung, Tetrahedron Lett. 2002, 43, 7899-7902.
270. H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron Lett. 2003, 44, 1541-1544.
271. a) E. Shirakawa, Y. Murota, Y. Nakao, T. Hiyama, Synlett 1997, 1143-1144;
272. b) L. Alcaraz, R. J. K. Taylor, Synlett 1997, 791-792.
273. K. M. Hossain, T. Kameyama, T. Shibata, K. Takagi, Bull. Chem. Soc. Jpn. 2001, 74, 2415-2420.
274. T. Ohe, T. Tanaka, M. Kuroda, C. S. Cho, K. Ohe, S. Uemura, Bull. Chem. Soc. Jpn. 1999, 72, 1851-1855.
275. C. W. Jones, Applications of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry, Cambridge, 1999.
276. a) V. N. Zudin, V. A. Likholobov, Y. I. Ermakov, Kinet. Katal. 1977, 18, 921-926;
277. b) V. N. Zudin, V. A. Likholobov, Y. I. Ermakov, Kinet. Katal. 1979, 20, 1599-1600.
278. R. C. Larock, Comprehensive Organic Transformations, 2nd ed., Wiley-VCH, New York, 1999, pp. 251-256.
279. Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013.
280. a) T. Nishimura, K. Ohe, S. Uemura, J. Am. Chem. Soc. 1999, 121, 2645-2646;
281. b) T. Nishimura, K. Ohe, S. Uemura, J. Org. Chem. 2001, 66, 1455-1465.
282. S.-B. Park, J. K. Cha, Org. Lett. 2000, 2, 147-149.
283. T. Nishimura, H. Araki, Y. Maeda, S. Uemura, Org. Lett. 2003, 5, 2997-2999.
284. For a discussion of synthetic and industrial applications of oxidative carbonylation, see: a) H. M. Colquhoun, D. J. Thompson, M. V. Twigg, Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum, New York, 1991;
285. b) A. Klausener, J.-D. Jentsch in reference [4b], pp. 164-182;
286. c) M. Beller, A. M. Tafesh in reference [4b], pp. 182-194.
287. a) G. P. Chiusoli, M. Costa, S. Reverberi, Synthesis 1989, 262-265;
288. b) B. Gabriele, M. Costa, G. Salerno, G. P. Chiusoli, J. Chem. Soc. Chem. Commun. 1992, 1007-1008;
289. c) B. Gabriele, M. Costa, G. Salerno, G. P. Chiusoli, J. Chem. Soc. Chem. Commun. 1994, 1429-1430;
290. d) B. Gabriele, M. Costa, G. Salerno, G. P. Chiusoli, J. Chem. Soc. Perkin Trans. 1 1994, 83-87;
291. e) A. Bonardi, M. Costa, B. Gabriele, G. Salerno, G. P. Chiusoli, Tetrahedron Lett. 1995, 36, 7495-7498;
292. f) B. Gabriele, G. Salerno, F. De Pascali, G. T. Sciano, M. Costa, G. P. Chiusoli, Tetrahedron Lett. 1997, 38, 6877-6880;
293. g) B. Gabriele, G. Salerno, F. De Pascali, M. Costa, G. P. Chiusoli, J. Chem. Soc. Perkin Trans. 1 1997, 147-154;
294. h) A. Bacchi, G. P. Chiusoli, M. Costa, C. Sani, B. Gabriele, G. Salerno, J. Organomet. Chem. 1998, 562, 35-43;
295. i) A. Fazio, B. Gabriele, G. Salerno, S. Destri, Tetrahedron 1999, 55, 485-502;
296. j) B. Gabriele, G. Salerno, D. Brindisi, M. Costa, G. P. Chiusoli, Org. Lett. 2000, 2, 625-627;
297. k) B. Gabriele, G. Salerno, F. De Pascali, M. Costa, G. P. Chiusoli, J. Organomet. Chem. 2000, 593-594, 409-415;
298. l) A. Bacchi, M. Costa, B. Gabriele, G. Pelizzi, G. Salerno, J. Org. Chem. 2002, 67, 4450-4457;
299. m) P. Gabriele, G. Salerno, A. Fazio, F. B. Campana, Chem. Commun. 2002, 1408-1409;
300. n) B. Gabriele, L. Veltri, G. Salerno, M. Costa, G. P. Chiusoli, Eur. J. Org. Chem. 2003, 1722-1728;
301. o) B. Gabriele, R. Mancuso, G. Salerno, M. Costa, Chem. Commun. 2003, 486-487;
302. p) B. Gabriele, R. Mancuso, G. Salerno, M. Costa, J. Org. Chem. 2003, 68, 601-604.
303. T. Iwasawa, M. Tokunaga, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2004, 126, ASAP article.
304. G.-J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal. 2003, 345, 1341-1352
305. J. T. Bagdanoff, B. M. Stoltz, Angew. Chem. 2004, 116, 357-361; Angew. Chem. Int. Ed. 2004, 43, 353-357.
306. J. T. Bagdanoff, B. M. Stoltz, Angew. Chem. 2004, 116, 357-361; Angew. Chem. Int. Ed. 2004, 43, 353-357.
307. R. M. Trend, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 4482-4483.
308. a) I. S. Ali, A. Sudalai, Tetrahedron Lett. 2002, 43, 5435-5436;
309. b) D. D. Caspi, D. C. Ebner, J. T. Bagdanoff, B. M. Stoltz, Adv. Synth. Catal. 2004, 346, 185-189.
310. S. Paavola, K. Zetterberg, T. Privalov, I. Csöregh, C. Moberg, Adv. Synth. Catal. 2004, 346, 237-244.
311. M. M. S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218-219.
312. B. Furman, M. Dziedzic, Tetrahedron Lett. 2003, 44, 8249-8252
313. C. Bee, E. Leclerc, M. A. Tius, Org. Lett. 2003, 5, 4927-4930.
314. M. Reiter, S. Ropp, V. Gouverneur, Org. Lett. 2004, 6, 91-94.
315. a) B. Gabriele, G. Salerno, M. Costa, G. P. Chiusoli, J. Organomet. Chem. 2003, 687, 219-228;
316. b) B. Gabriele, G. Salerno, P. Plastina, M. Costa, A. Crispini, Adv. Synth. Catal. 2004, 346, 351-358;
317. c) A. Bacchi, M. Costa, N. Della Cà, M. Fabbricatore, A. Fazio, B. Gabriele, C. Nasi, G. Salerno, Eur. J. Org. Chem. 2004, 574-585;
318. d) M. Costa, N. Della Cà, B. Gabriele, C. Massera, G. Salerno, M. Soliani, J. Org. Chem. 2004, 69, 2469-2477.