A modular approach to structurally diverse bidentate chelate ligands for transition metal catalysis

Chemistry - A European Journal

Volumn 6, Issue 15, 2000, Pages 2874-2894

  Kranich, Remo ^a   Eis, Knut ^a   Geis, Oliver ^a   Mühle, Stefan ^a   Bats, Jan W ^b   Schmalz, Hans Günther ^a,c  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b GOETHE UNIVERSITY   (Germany)

^c UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Hydroquinones; P ligands; Palladium; Synthesis design

Indexed keywords

HYDROQUINONE DERIVATIVE; LIGAND; METAL COMPLEX;

AMINATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 0034604496     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000804)6:15<2874::AID-CHEM2874>3.0.CO;2-1     Document Type: Article

References (119)

1. a) Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 and 2 (Eds. B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996;
2. b) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048;
3. b) W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048;
4. c) Transition Metals for Organic Synthesis, Vol. 1 and 2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998.
5. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994;
6. b) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis, VCH, Weinheim, 1993;
7. c) B. M. Trost, D. L. van Vranken, Chem. Rev. 1996, 96, 395.
8. G. Quinkert, H. Bang, D. Reichert, Helv. Chim. Acta 1996, 79, 1260.
9. For selected recent examples, see : a) S. R. Gilbertson, C.-W. T. Chang, Chem. Commun. 1997, 975;
10. b) K. Boog-Wick, P. S. Pregosin, G. Trabesinger, Organometallics 1998, 17, 3254;
11. c) M. T. Reetz, T. Neugebauer, Angew. Chem. 1999, 111, 134; Angew. Chem. Int. Ed. 1999, 38, 179;
12. c) M. T. Reetz, T. Neugebauer, Angew. Chem. 1999, 111, 134; Angew. Chem. Int. Ed. 1999, 38, 179;
13. d) J. J. A. Perea, A. Borner, P. Knochel, Tetrahedron Lett. 1998, 39, 8073;
14. e) J. P. Cahill, P. J. Guiry, Tetrahedron: Asymmetry 1998, 9, 4301;
15. f) X. Bei, T. Uno, J. Norris, H. W. Turner, W. H. Weinberg, A. S. Guram, J. L. Petersen, Organometallics 1999, 18, 1840, and references cited therein.
16. a) T. Hayashi in Ferrocenes (Eds.: A. Togni, T. Hayashi), VCH, Weinheim, 1995, p. 105;
17. b) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475;
18. b) A. Togni, Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475;
19. for a recent review, see: c) C. J. Richards, A. J. Locke, Tetrahedron Asymmetry 1998, 9, 2377.
20. a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614; Angew. Chem. Int. Ed. Engl. 1993, 32, 655;
21. a) P. von Matt, A. Pfaltz, Angew. Chem. 1993, 105, 614; Angew. Chem. Int. Ed. Engl. 1993, 32, 655;
22. b) J. Sprinz, G. Helmchen, Tetrahedron Lett. 1993, 34, 1769;
23. c) G. J. Dawson, C. G. Frost, J. M. J. Williams, S. J. Coote, Tetrahedron Lett. 1993, 34, 3149;
24. for a very recent contribution, see: d) H. Takada, K. Ohe, S. Uemura, Angew. Chem. 1999, 111, 1367; Angew. Chem. Int. Ed. 1999, 38, 1288.
25. for a very recent contribution, see: d) H. Takada, K. Ohe, S. Uemura, Angew. Chem. 1999, 111, 1367; Angew. Chem. Int. Ed. 1999, 38, 1288.
26. a) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345;
27. b) K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiushi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413, and references cited therein;
28. c) Y. Uozumi, A. Tanahashi, S.-Y. Lee, T. Hayashi, J. Org. Chem. 1993, 58, 1945;
29. d) B. H. Lipshutz, Y.-J. Shin, Tetrahedron Lett. 1998, 39, 7017;
30. d) K. Selvakumar, M. Valentini, M. Wörle, P. S. Pregosin, A. Albinati, Organometallics 1999, 18, 1207.
31. a) Chem. Rev. 1997, 97, 347-510;
32. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288;
33. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288;
34. c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555;
35. d) D. R. Lin, P. G. Schultz, Angew. Chem. 1999, 111, 37; Angew. Chem. Int. Ed. 1999, 38, 36.
36. d) D. R. Lin, P. G. Schultz, Angew. Chem. 1999, 111, 37; Angew. Chem. Int. Ed. 1999, 38, 36.
37. a) G. Liu, J. A. Ellman, J. Org. Chem. 1995, 60, 7712;
38. b) K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. 1996, 108, 192; Angew. Chem. Int. Ed. Engl. 1996, 35, 220;
39. b) K. Burgess, H.-J. Lim, A. M. Porte, G. A. Sulikowski, Angew. Chem. 1996, 108, 192; Angew. Chem. Int. Ed. Engl. 1996, 35, 220;
40. c) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475;
41. d) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668;
42. d) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776; Angew. Chem. Int. Ed. Engl. 1996, 35, 1668;
43. e) M. B. Francis, N. S. Finney, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 8983;
44. f) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782; Angew. Chem. Int. Ed. Engl. 1997, 36, 1704;
45. f) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782; Angew. Chem. Int. Ed. Engl. 1997, 36, 1704;
46. g) S. J. Taylor, J. P. Morken, Science 1998, 280, 267;
47. h) M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2192.; Angew. Chem. Int. Ed. 1998, 37, 2647;
48. h) M. T. Reetz, M. H. Becker, K. M. Kühling, A. Holzwarth, Angew. Chem. 1998, 110, 2192.; Angew. Chem. Int. Ed. 1998, 37, 2647;
49. i) A. C. Cooper, L. H. McAlexander, D.-H. Lee, M. T. Torres, R. H. Crabtree, J. Am. Chem. Soc. 1998, 120, 9971;
50. j) A. M. Porte, K. Burgess, J. Am. Chem. Soc. 1998, 120, 9180;
51. k) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901;
52. 1) C. Gennari, S. Ceccarelli, U. Piarulli, C. A. G. N. Montalbetti, R. F. W. Jackson, J. Org. Chem. 1998, 63, 5312;
53. m) T. R. Boussie, C. Coutard, H. Turner, V. Murphy, T. S. Powers, Angew. Chem. 1998, 111, 3472; Angew. Chem. Int. Ed. 1998, 37, 3272;
54. m) T. R. Boussie, C. Coutard, H. Turner, V. Murphy, T. S. Powers, Angew. Chem. 1998, 111, 3472; Angew. Chem. Int. Ed. 1998, 37, 3272;
55. n) T. R. Boussie, V. Murphy, K. A. Hall, C. Coutard, C. Dales, M. Petro, E. Carlson, H. W. Turner, T. S. Powers, Tetrahedron 1999, 55, 11699;
56. o) A. Berkessel, D. A. Hérault, Angew. Chem. 1999, 111, 99; Angew. Chem. Int. Ed. 1999, 38, 102;
57. o) A. Berkessel, D. A. Hérault, Angew. Chem. 1999, 111, 99; Angew. Chem. Int. Ed. 1999, 38, 102;
58. p) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519; Angew. Chem. Int. Ed. 1999, 38, 497;
59. p) K. Ding, A. Ishii, K. Mikami, Angew. Chem. 1999, 111, 519; Angew. Chem. Int. Ed. 1999, 38, 497;
60. q) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987; Angew. Chem. Int. Ed. 1999, 38, 937;
61. q) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987; Angew. Chem. Int. Ed. 1999, 38, 937;
62. r) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284.
63. For reviews and general treatments, see: a) S. Borman, Chem. Eng. News 1996, November 4, 37;
64. b) C. Gennari, H. P. Nestler, U. Piarulli, B. Salmon, Liebigs Ann./Recueil 1997, 637;
65. c) W. H. Weinberg, B. Jandeleit, K. Self, H. Turner, Curr. Opin. Solid State Mater. Sci. 1998, 3, 104;
66. d) H. Kagan, J. Organomet. Chem. 1998, 567, 3;
67. e) P. M. Morse, Chem. Eng. News 1998, December 7, 25;
68. f) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648; Angew. Chem. Int. Ed. 1999, 38, 2494.
69. f) B. Jandeleit, D. J. Schaefer, T. S. Powers, H. W. Turner, W. H. Weinberg, Angew. Chem. 1999, 111, 2648; Angew. Chem. Int. Ed. 1999, 38, 2494.
70. W. H. Weinberg, E. McFarland, I. Goldwasser, T. Boussie, H. Turner, J. A. M. Van Beek, V. Murphy, T. Powers, (PCT Intl. Appl.) WO98/ 03521 [Chem. Abstr. 1998, 128, 141181h].
71. a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Chemistry, 2nd ed., Wiley, New York, 1991;
72. b) P. G. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994.
73. V. Snieckus, Chem. Rev. 1990, 90, 879;
74. b) H. W. Gschwend, H. R. Rodriguez, Org. React. 1976, 26, 1.
75. D. J. Dodsworth, M.-P. Calcagno, E. U. Ehrmann, B. Devadas, P. G. Sammes, J. Chem. Soc. Perkin Trans. 1 1981, 2120.
76. G. A. Olah, S. C. Narang, B. G. B. Gupta, R. Malhotra, J. Org. Chem. 1979, 44, 1979.
77. 2. In this case, the migration of the TBS group from the oxygen to the metallated carbon occured even at very low temperatures; for the use of di-anionic intermediates for the synthesis of o-phosphanylphenol derivatives, see: J. Heinicke, R. Kadyrov, M. K. Kindermann, M. Koesling, P. G. Jones, Chem. Ber. 1996, 129, 1547.
78. a) V. N. Kalinin, Synthesis 1992, 413;
79. for recent monographs, see: b) L. Brandsma, S. F. Vasilevsky, H. D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer, Berlin, Heidelberg 1998;
80. c) Metal-Catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998.
81. For a comprehensive review, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
82. for the combination of ortho-metallation/Suzuki-coupling, see: b) M. J. Sharp, W. Cheng, V. Snieckus, Tetrahedron Lett. 1987, 43, 5093.
83. T. Watanabe, N. Miyaura, A. Suzuki, Synlett 1992, 207.
84. a) J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215;
85. b) S. Wagaw, R. A. Rennels, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 8451;
86. c) S. Wagaw, S. L. Buchwald, J. Org. Chem. 1996, 61, 7240;
87. for a review, see: d) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805.
88. a) M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 7217;
89. for reviews, see: b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154; Angew. Chem. Int. Ed. 1998, 37, 2046;
90. for reviews, see: b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154; Angew. Chem. Int. Ed. 1998, 37, 2046;
91. c) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852
92. Only the deprotected (phenolic) starting materials were isolated.
93. a) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722;
94. b) M. C. Harris, O. Geis, S. L. Buchwald, J. Org. Chem. 1999, 64, 6019.
95. The MOM protecting group plays an important role for the success of these reactions, see O. Geis and H.-G. Schmalz, unpublished results.
96. a) D. R. Williams, B. A. Barner, K. Nishitani, J. G. Philipps, J. Am. Chem. Soc. 1982, 104, 4708;
97. the cleavage of the MOM group in substituted o-phosphanylphenols was first described by: b) A. Kless, C. Lefeber, A. Spannenberg, R. Kempe, W. Baumann, J. Holz, A. Börner, Tetrahedron 1996, 52, 14599.
98. III electrophiles of type 13 according to Scheme 8: from diols: a) M. J. Baker, P. G. Pringle, J. Chem. Soc. Chem. Commun. 1991, 1292;
99. b) N. Greene, T. P. Kee, Synth. Commun. 1993, 23, 1651;
100. c) J.-M. Brunel, O. Pardigon, M. Maffei, G. Buono, Tetrahedron: Asymmetry 1992, 3, 1243;
101. d) M. T. Reetz, T. Neugebauer, Angew. Chem. 1999, 111, 134; Angew. Chem. Int. Ed. 1999, 38, 179;
102. d) M. T. Reetz, T. Neugebauer, Angew. Chem. 1999, 111, 134; Angew. Chem. Int. Ed. 1999, 38, 179;
103. from aminoalcohols: e) S. D. Pastor, R. K. Rodebaugh, P. A. Odorisio, B. Pugin, G. Rihs, A. Togni, Helv. Chim. Acta 1991, 74, 1175;
104. for the synthesis of chiral phosphites derived from TADDOL, see: f) J.-i. Sakaki, B. Schweizer, D. Seebach, Helv. Chim. Acta 1993, 76, 2654.
105. T. König, W. D. Habicher, U. Hähner, J. Pionteck, C. Rüger, K. Schwetlick, J. Prakt. Chem. 1992, 334, 333.
106. H. M. Colquhoun, J. Holton, D. Thompson, M. V. Twigg, New Pathways for Organic Synthesis, Plenum, New York, London, 1984.
107. -3. The calculations were performed with the SMART, SHELX, and MolEN program systems. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-137394. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
108. a) K. Aurivillius, G.-I. Bertinsson, Acta Crystallogr. Sect. B 1981, 37, 2073;
109. b) S.-T. Liu, C. L. Cheng, M. C. Cheng, S.-M. Peng, Polyhedron 1990, 9, 2579;
110. c) S. Y. M. Chooi P.-H. Leung, K. F. Mok, Inorg. Chim. Acta 1993, 205, 245;
111. d) K. Sunkel, A. Blum, Z. Naturforsch. Teil B 1995, 50, 1307.
112. 2 = 0.150, S = 1.03. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-132471. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
113. E. Vedejs, J. Org. Chem. 1978, 43, 188.
114. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
115. D. M. Daddwell, D. T. Pegg, M. R. Bendall, J. Magn. Reson. 1982, 48, 323.
116. The spectroscopic data of compound 2 a are in accordance with those reported by: A. Stern, J. S. Swenton, J. Org. Chem. 1987, 52, 2763.
117. M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 1977, 42, 3772.
118. D. J. Dodsworth, M.-P. Calcagno, E. U. Ehrmann, B. Devadas, P. G. Sammes, J. Am. Chem. Soc. Perkin Trans. 1 1981, 2120.
119. M. Suzuki, Y. Kimura, S. Terashima, Bull. Chem. Soc. Jpn. 1986, 59, 3559.