Progress in the palladium-catalyzed cyanation of aryl chlorides

Chemistry - A European Journal

Volumn 9, Issue 8, 2003, Pages 1828-1836

  Sundermeier, Mark ^a   Zapf, Alexander ^a   Mutyala, Sateesh ^a   Baumann, Wolfgang ^a   Sans, Jürgen ^b   Weiss, Stefan ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

Author keywords

Aryl chlorides; Benzonitriles; Cyanation; Homogeneous catalysis; Palladium

Indexed keywords

ADDITION REACTIONS; AMINES; CATALYST ACTIVITY; CHELATION; OXIDATION; PALLADIUM;

CYANATION;

CHLORINE COMPOUNDS;

1,4 BIS(DIPHENYLPHOSPHINO)BUTANE; 1,5 BIS(DIPHENYLPHOSPHINO)PENTANE; AMINE; ANTIANDROGEN; ANTIDEPRESSANT AGENT; ANTINEOPLASTIC AGENT; AROMATASE INHIBITOR; BENZONITRILE; BICALUTAMIDE; CHLORIDE; CITALOPRAM; CYAMEMAZINE; CYANIDE; FADROZOLE; HALIDE; LETROZOLE; LIGAND; METAL COMPLEX; NEUROLEPTIC AGENT; NEUTROMIL; PALLADIUM COMPLEX; PERICIAZINE; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; SEROTONIN UPTAKE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYANATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0038669308     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390210     Document Type: Article

References (99)

1. a) J. G., de Vries, Can. J. Chem. 2001, 79, 1086-1092;
2. b) M. Beller, A. Zapf, W. Mägerlein, Chem. Eng. Technol. 2001, 24, 575-582;
3. c) A. Zapf, M. Beller, Top. Catal. 2002, 19, 101-109.
4. a) W. A. Herrmann, C, Broßmer, K. Öfele, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
5. a) W. A. Herrmann, C, Broßmer, K. Öfele, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
6. b) M. Beller, H. Fischer, W. A. Herrmann, C. Broßmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849;
7. b) M. Beller, H. Fischer, W. A. Herrmann, C. Broßmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849;
8. c) M. Beller, T. H. Riermeier, S. Haber, H.-J. Kleiner, W. A. Herrmann, Chem. Ber. 1996, 129, 1259-1264;
9. d) M. Beller, T. H. Riermeier, Tetrahedron Lett. 1996, 37, 6535-6538;
10. e) W A. Herrmann, C. Broßmer, C.-P. Reisinger, K. Öfele, M. Beller, T. H. Riermeier, Chem. Eur. J. 1997, 3, 1357-1364;
11. f) M. Beller, T. H. Riermeier, C.-P. Reisinger, W. A. Herrmann, Tetrahedron Lett. 1997, 38, 2073-2074;
12. g) M. Beller, T. H. Riermeier, Eur. J. Inorg. Chem. 1998, 29-35;
13. h) M. Beller, T. H. Riermeier, W. Mägerlein, T. E. Müller, W. Scherer, Polyhedron 1998, 17, 1165-1176;
14. i) G. Stark, T. H. Riermeier, M. Beller, Synth. Commun. 2000, 30, 1703-1711;
15. j) A. Zapf, M. Beller, Chem. Eur. J. 2001, 7, 2908-2915.
16. a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 38, 3387-3388;
17. a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 38, 3387-3388;
18. b) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723;
19. c) J. P. Wolfe, S. L. Buchwald, Angew. Chem. 1999, 111, 2570-2573; Angew. Chem. Int. Ed. 1999, 39, 2413-2416;
20. c) J. P. Wolfe, S. L. Buchwald, Angew. Chem. 1999, 111, 2570-2573; Angew. Chem. Int. Ed. 1999, 39, 2413-2416;
21. d) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561;
22. e) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803;
23. f) A. F. Littke, G. C. Fu, J. Org. Chem. 1999, 64, 10-11;
24. g) K. H. Shaughnessy, P. Kim, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 2123-2132;
25. h) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575-5580;
26. i) X. Bei, T. Uno, J. Norris, H. W. Turner, W. H. Weinberg, A. S. Guram, Organometallics 1999, 18, 1840-1853;
27. j) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028;
28. k) J. P. Wolfe, H. Tomori, J. P. Sadighi, J. J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158-1174;
29. l) M. Gómez Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476;
30. m) S.-Y. Liu, M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409;
31. n) A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989-7000;
32. o) L. M. Alcazar-Roman, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 12905-12906;
33. p) G. Y. Li, Angew. Chem. 2001, 113, 1561-1564; Angew. Chem. Int. Ed. 2001, 40, 1513-1516;
34. p) G. Y. Li, Angew. Chem. 2001, 113, 1561-1564; Angew. Chem. Int. Ed. 2001, 40, 1513-1516;
35. q) M. L. Clark, D. J. Cole-Hamilton, J. D. Woollins, J. Chem. Soc. Dalton Trans. 2001, 2721-2723;
36. r) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541;
37. s) M. Feuerstein, H. Doucet, M. Santelli, J. Org. Chem. 2001, 66, 5923-5925;
38. t) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131-209, and references therein;
39. u) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
40. u) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
41. v) G. Y. Li, W. J. Marshall, Organometallics 2002, 21, 590-591.
42. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155.
43. A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155.
44. A. Ehrentraut, A. Zapf, M. Beller, Synlett 2000, 1589-1592.
45. A. Ehrentraut, A. Zapf, M. Beller, J. Mol. Cat. 2002, 182-183, 515-523.
46. A. Ehrentraut, A. Zapf, M. Beller, Adv. Synth. Cat. 2002, 344, 209-217.
47. a) W. Mägerlein, A. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940-2943; Angew. Chem. Int. Ed. 2001, 40, 2856-2859;
48. a) W. Mägerlein, A. Indolese, M. Beller, Angew. Chem. 2001, 113, 2940-2943; Angew. Chem. Int. Ed. 2001, 40, 2856-2859;
49. b) M. Beller, W. Mägerlein, A. F. Indolese, C. Fischer, Synthesis 2001, 1098-1109;
50. c) M. Beller, A. F. Indolese, Chimia 2001, 55, 684-687;
51. d) W. Mägerlein, A. F. Indolese, M. Beller, J. Organomet. Chem. 2002, 641, 30-40.
52. a) J. Huang, G. Grasa, S. P. Nolan, Org. Lett. 1999, 1, 1307-1309;
53. b) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805;
54. c) C. Zhang, M. L. Trudell, Tetrahedron Lett. 2000, 41, 595-598;
55. d) M. C. Done, T. Ruther, K. J. Cavell, M. Kilner, E. J. Peacock, N. Braussaud, B. W. Skelton, A. White, J. Organomet. Chem. 2000, 607, 78-92;
56. e) A. Fürstner, A. Leitner, Synlett 2001, 2, 290-292;
57. f) W. A. Herrmann, V. P. W. Böhm, C. W. K. Gstöttmayr, M. Grosche, C.-P. Reisinger, T. Weskamp, J. Organomet. Chem. 2001, 617, 616-628, and references therein;
58. g) D. S. McGuinness, N. Saendig, B. F. Yates, K. J. Cavell, J. Am. Chem. Soc. 2001, 123, 4029-4040;
59. h) C. J. Mathews, P. J. Smith, T. Welton, A. J. P. White, D. J. Williams, Organometallics 2001, 20, 3848-3850;
60. i) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201-202;
61. j) G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics 2002, 21, 2866-2873;
62. k) A. C. Hillier, G. A. Grasa, M. S. Viciu, M. H. Lee, C. Yang, S. P. Nolan, J. Organomet. Chem. 2002, 653, 69-82;
63. l) A. C. Hillier, S. P. Nolan, Platinum Metals Rev. 2002, 46, 50-64, and references therein;
64. m) K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 2002, 4, 3031-3033.
65. A. Kleemann, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed., Thieme, Stuttgart, 2001, pp. 241, 488, 553, 825, 1154, 1598.
66. a) F. Hagedorn, H.-P. Gelbke in Ullmanns Encyklopädie der Technischen Chemie, Vol. 17 (Eds.: E. Bartholomé, E. Biekert, H. Hellmann, H. Ley, W. M. Weigert, E. Weise), 4th ed., Verlag Chemie, Weinheim, 1979, pp. 333-338;
67. b) G. P. Ellis, T. M. Romney-Alexander, Chem. Rev. 1987, 87, 779-794.
68. For the nickel-catalyzed cyanation of aryl halides, see: a) L. Cassar, M. Foà, F. Montanari, G. P. Marinelli, J. Organomet. Chem. 1979, 173, 335-339; b) Y. Sakakibara, F. Okuda, A. Shimoyabashi, K. Kirino, M. Sakai, N. Uchino, K. Takagi, Bull. Chem. Soc. Jpn. 1988, 61, 1985-1990; c) Y. Sakakibara, Y. Ido, K. Sasaki, M. Sakai, N. Uchino, Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778; M.-H. Rock, A. Merhold (Bayer AG), WO 98/37058, 1998.
69. For the nickel-catalyzed cyanation of aryl halides, see: a) L. Cassar, M. Foà, F. Montanari, G. P. Marinelli, J. Organomet. Chem. 1979, 173, 335-339; b) Y. Sakakibara, F. Okuda, A. Shimoyabashi, K. Kirino, M. Sakai, N. Uchino, K. Takagi, Bull. Chem. Soc. Jpn. 1988, 61, 1985-1990; c) Y. Sakakibara, Y. Ido, K. Sasaki, M. Sakai, N. Uchino, Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778; M.-H. Rock, A. Merhold (Bayer AG), WO 98/37058, 1998.
70. For the nickel-catalyzed cyanation of aryl halides, see: a) L. Cassar, M. Foà, F. Montanari, G. P. Marinelli, J. Organomet. Chem. 1979, 173, 335-339; b) Y. Sakakibara, F. Okuda, A. Shimoyabashi, K. Kirino, M. Sakai, N. Uchino, K. Takagi, Bull. Chem. Soc. Jpn. 1988, 61, 1985-1990; c) Y. Sakakibara, Y. Ido, K. Sasaki, M. Sakai, N. Uchino, Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778; M.-H. Rock, A. Merhold (Bayer AG), WO 98/37058, 1998.
71. For the nickel-catalyzed cyanation of aryl halides, see: a) L. Cassar, M. Foà, F. Montanari, G. P. Marinelli, J. Organomet. Chem. 1979, 173, 335-339; b) Y. Sakakibara, F. Okuda, A. Shimoyabashi, K. Kirino, M. Sakai, N. Uchino, K. Takagi, Bull. Chem. Soc. Jpn. 1988, 61, 1985-1990; c) Y. Sakakibara, Y. Ido, K. Sasaki, M. Sakai, N. Uchino, Bull. Chem. Soc. Jpn. 1993, 66, 2776-2778; M.-H. Rock, A. Merhold (Bayer AG), WO 98/37058, 1998.
72. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
73. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
74. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
75. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
76. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
77. For the palladium-catalyzed cyanation of aryl halides, see: a) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1975, 48, 3298-3301; b) K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, N. Hayama, Bull. Chem. Soc. Jpn. 1976, 49, 3177-3180; c) J. R. Dalton, S. L. Regen, J. Org. Chem. 1979, 44, 4443-4444; d) Y. Akita, M. Shimazaki, A. Ohta, Synthesis 1981, 974-975; e) Y. Anderson, B. Långström, J. Chem. Soc. Perkin Trans. I 1994, 1395-1400; f) B. A. Anderson, E. C. Bell, F. O. Ginah, N. K. Harn, L. M. Pagh, J. P. Wepsiec, J. Org. Chem. 1998, 63, 8224-8228.
78. H. Hugl (Bayer AG), Presentation at the conference 50 Years of Catalysis Research in Rostock, July 1-3 2002, Rostock; see also: a) M.-H. Rock, A. Merhold (Bayer AG), DE 197 06 648 A1, 1997; b) M.-H. Rock, A. Merhold (Bayer AG), US 6162942, 2000.
79. H. Hugl (Bayer AG), Presentation at the conference 50 Years of Catalysis Research in Rostock, July 1-3 2002, Rostock; see also: a) M.-H. Rock, A. Merhold (Bayer AG), DE 197 06 648 A1, 1997; b) M.-H. Rock, A. Merhold (Bayer AG), US 6162942, 2000.
80. H. Hugl (Bayer AG), Presentation at the conference 50 Years of Catalysis Research in Rostock, July 1-3 2002, Rostock; see also: a) M.-H. Rock, A. Merhold (Bayer AG), DE 197 06 648 A1, 1997; b) M.-H. Rock, A. Merhold (Bayer AG), US 6162942, 2000.
81. F. Jin, P. N. Confalone, Tetrahedron Lett. 2000, 41, 3271-3273.
82. M. Sundermeier, A. Zapf, M. Beller, J. Sans, Tetrahedron Lett. 2001, 42, 6707-6710.
83. A. J. Ewins, US 2510047, 1950.
84. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
85. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
86. b) C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314-321;
87. c) C. Amatore, A. Jutand, A. Thuilliez, Organometallics 2001, 20, 3241-3249;
88. d) E. Galardon, S. Ramdeehul, J. M. Brown, A. Cowley, K. K. M. Hii, A. Jutand, Angew. Chem. 2002, 114, 1838-1841; Angew. Chem. Int. Ed. 2002, 41, 1760-1763.
89. d) E. Galardon, S. Ramdeehul, J. M. Brown, A. Cowley, K. K. M. Hii, A. Jutand, Angew. Chem. 2002, 114, 1838-1841; Angew. Chem. Int. Ed. 2002, 41, 1760-1763.
90. V. V. Grushin, H. Alper in Topics in Organometallic Chemistry Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, Berlin, 1999, pp. 193-226.
91. a) M. Beller, H. Fischer, K. Kühlein, C.-P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257-259;
92. b) M. T. Reetz, E. Westermann, Angew. Chem. 2000, 112, 170-173; Angew. Chem. Int. Ed. 2000, 39, 165-168.
93. b) M. T. Reetz, E. Westermann, Angew. Chem. 2000, 112, 170-173; Angew. Chem. Int. Ed. 2000, 39, 165-168.
94. K. Takagi, T. Okamoto, Y. Sakakibara, S. Oka, Chem. Lett. 1973, 471-474.
95. 31P NMR experiment, seems to result from the NMR apparatus used.
96. a) K.-C. Kong, C.-H. Cheng, J. Am. Chem. Soc. 1991, 113, 6313-6315;
97. b) W. A. Herrmann, C. Broßmer, K. Öfele, M. Beller, H. Fischer, J. Organomet. Chem. 1995, 491, C1-C4;
98. c) V. V. Grushin, Organometallics 2000, 19, 1888-1900.
99. The concentration of cyanide in solution is influenced by the solvent purity and the size of the KCN crystals. Indeed, when we used different charges of KCN (same purity, same supplier), reproducibility was sometimes a problem. By measuring the crystallite size we discovered that 120 nm KCN crystals gave much better results than 60 nm KCN crystallites. All catalytic experiments described in this paper were performed with 120 nm KCN and we recommend use of this crystallite size.