Transition-metal-catalyzed benzylation of arenes and heteroarenes

Angewandte Chemie - International Edition

Volumn 44, Issue 2, 2004, Pages 238-242

  Mertins, Kristin ^a   Iovel, Irina ^a   Kischel, Jette ^a   Zapf, Alexander ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Arenes; Benzylation; Friedel Crafts reaction; Iridium; Platinum

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; BENZENE; CARBON DIOXIDE; CATALYSTS; IRIDIUM; PALLADIUM; PLATINUM; RHODIUM;

BENZYLATION; BENZYLIC ACETATES; HETEROARENES; MILD REACTION CONDITIONS;

TRANSITION METALS;

IRIDIUM; PALLADIUM; PLATINUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; TRANSITION ELEMENT; BENZENE DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; XYLENE;

ARTICLE; BENZYLATION; CATALYSIS; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

BENZENE DERIVATIVES; CATALYSIS; IRIDIUM; MOLECULAR STRUCTURE; PALLADIUM; PHENYLACETATES; PLATINUM; XYLENES;

EID: 11844269291     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460666     Document Type: Article

References (71)

1. K. Weissermel, H.-J. Arpe, Industrielle Organische Chemie, VCH, Weinheim, 1988.
2. a) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatami, M. Sonoda, N. Chatani, Nature 1993, 366, 529-531;
3. b) F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatami, M. Sonoda, N. Chatani, S. Murai, Bull. Chem. Soc. Jpn. 1995, 68, 62-83;
4. c) F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826-834;
5. d) F. Kakiuchi, T. Uetsuhara, Y. Tanaka, N. Chatani, S. Murai, J. Mol. Catal. 2002, 182, 511-514;
6. e) Y. Guari, A. Castellanos, S. Sabo-Etienne, B. Chaudret, J. Mol. Catal. 2004, 222, 77-82.
7. a) F. Kakiuchi, M. Yamauchi, N. Chatani, S. Murai, Chem. Lett. 1996, 111-112;
8. b) C-H. Jun, J.-B. Hong, Y-H. Kim, K.-Y Chung, Angew. Chem. 2000, 772, 3582-3584; Angew. Chem. Int. Ed. 2000, 39, 3440-3442;
9. b) C-H. Jun, J.-B. Hong, Y-H. Kim, K.-Y Chung, Angew. Chem. 2000, 772, 3582-3584; Angew. Chem. Int. Ed. 2000, 39, 3440-3442;
10. c) C.-H. Jun, C. W. Moon, J-B. Hong, S.-G. Lim, K.-Y. Chung, Y-H. Kim, Chem. Eur. J. 2002, 8, 485-492;
11. d) Y-G. Lim, J.-S. Han, B. T. Koo, J.-B. Kang, J. Mol. Catal. 2004, 209, 41-49.
12. For a recent review on stereoselective Friedel-Crafts-type reactions see: M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556.
13. For a recent review on stereoselective Friedel-Crafts-type reactions see: M. Bandini, A. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556.
14. a) R. K. Thalji, K. A. Ahrendt, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2001, 123, 9692-9693;
15. b) K. A. Ahrend, R. G. Bergman, J. A. Ellman, Org. Lett. 2003, 5, 1301-1303.
16. a) F. Kakiuchi, Y. Yamamoto, N. Chatani, S, Murai, Chem. Lett. 1995, 681-682;
17. b) C. G. Jia, W. T. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc. 2000, 122, 7252-7263;
18. c) T. Kitamura, K. Yamamoto, M. Kotani, J. Oyamada, C. Jia, Y. Fujiwara, Bull. Chem. Soc. Jpn. 2003, 76, 1889-1895.
19. a) E. J. Moore, W. R. Pretzer, T. J. O'Connell, J. Harris, L, Labounty, L. Chou, S. S. Grimmer, J. Am. Chem. Soc. 1992, 114, 5888-5890;
20. b) N. Chatani, T. Fukuyama, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 1996, 118, 493-494.
21. a) S. J. Pastine, S. W. Youn, D. Sames, Tetrahedron 2003, 59, 8859-8868;
22. b) S. J. Pastine, D. Sames, Org. Lett. 2003, 5, 4053-4055;
23. c) S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055-1058.
24. a) B. Sezen, D. Sames, Org. Lett. 2003, 5, 3607-3610;
25. b) B. Sezen, D. Sames, J. Am. Chem. Soc. 2003, 125, 5274-5275;
26. c) B. Sezen, D. Sames, J. Am. Chem. Soc. 2003, 125, 10580-10585.
27. For recent examples see : a) F. Rataboul, A. Zapf, R. Jackstell, S. Harkal, T. Riermeier, A. Monsees, U. Dingerdissen, M. Beller, Chem. Eur. J. 2004, 10, 2983-2990;
28. b) A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, M. Beller, Chem. Commun. 2004, 38-39;
29. c) A. Frisch, A. Zapf, O. Briel, B. Kayser, N. Shaikh, M. Beller, J. Mol. Catal. 2004, 214, 231-239;
30. d) K. Kumar, D. Michalik, I. Garcia Castro, A. Tillack, A. Zapf, M. Arlt, T. Heinrich, H. Böttcher, M. Beller, Chem. Eur. J. 2004, 10, 746-757;
31. e) M. Sundermeier, A. Zapf, M. Beller, Angew. Chem. 2003, 115, 1700-1703; Angew. Chem. Int. Ed. 2003, 42, 1661-1664;
32. e) M. Sundermeier, A. Zapf, M. Beller, Angew. Chem. 2003, 115, 1700-1703; Angew. Chem. Int. Ed. 2003, 42, 1661-1664;
33. f) K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 2002, 4, 3031-3033;
34. g) A. Ehrentraut, A. Zapf, M. Beller, J. Mol. Catal 2002, 182-183, 515-523;
35. h) A. Zapf, M. Beller, Top. Catal. 2002, 19, 101-109;
36. i) W. Mägerlein, A. F. Indolese, M. Beller, J. Organomet. Chem. 2002, 641, 30-40.
37. a) M. G. -Nordberg, K. Kolmodin, J. Aquist, S. F. Queener, A. Hallberg, J. Med. Chem. 2001, 44, 2391-2402;
38. b) H. H. Sun, V. J. Paul, W. Fenical, Phytochemistry 1983, 22, 743-745;
39. c) H. Hoshina, K. Maekawa, K. Taie, T. Igarashi, T. Sakurai, Heterocycles 2003, 60, 1779-1786;
40. d) C. Manzoni, M. R. Lovati, A. Bonelli, G. Galli, C. R. Sirtori, Eur. J. Pharmacol. 1990, 790, 39-49;
41. e) C. Rose, O. Vtoraya, A. Pluzanska, N. Davidson, M. Gershanovich, R. Thomas, S. Johnson, J. J. Caicedo, H. Gervasio, G. Manikhas, F. B. Ayed, S. B. -Radoux, H. A. C. Ross, R. Lang, Eur. J. Cancer 2003, 39, 2318-2327.
42. a) J. Jacob, L. Oldridge, J. Y. Zhang, M. Gaal, E. J. W. List, A. C. Grimsdale, K. Mullen, Curr. Cancer Drug Targets 2004, 4, 339-342;
43. b) M. S. Khan, M. R. A. Al-Mandhary, M. K. Al-Suti, B. Ahrens, M. F. Mahon, L. Male, P. R. Raithby, C. E. Boothby, A. Kohler, J. Chem. Soc. Dalton Trans. 1 2003, 74-84;
44. c) P. J. Skabara, I. M. Serebryako, I. F. Perepichka, Synth. Met. 1999, 102, 1336-1337.
45. a) G. A. Olah, R. Krishnamurti, G. K. S. Prakash in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 293-339;
46. b) R. M. Roberts, A. A. Khalaf, Friedel-Crafts Alkylation Chemistry, Marcel Dekker, New York, 1984;
47. c) Friedel-Crafts Chemistry (Ed.: G. A. Olah), Wiley, New York, 1973.
48. a) M. Noji, T. Ohno, K. Fuji, N. Futabe, H. Tajima, K. Ishii, J. Org. Chem. 2003, 68, 9340-9347;
49. b) T. Mukaiyama, H. Kamiyama, H. Yamanaka, Chem, Lett. 2003, 32, 814-815;
50. c) I. Shiina, M. Suzuki, Tetrahedron Lett. 2002, 43, 6391-6394;
51. d) G. V. M. Sharma, A. K. Mahalingam, J. Org. Chem. 1999, 64, 8943-8944;
52. e) T. Tsuchimoto, K. Tobita, T. Hiyama, S.-I. Fukuzawa, J. Org. Chem. 1997, 62, 6997-7005;
53. f) S.-I. Fukuzawa, T. Tsuchimoto, T Hiyama, J. Org. Chem. 1997, 62, 151-156;
54. g) M. T. E. Gihani, H. Heaney, K. F. Shuhaibar, Synlett 1996, 871-872.
55. Selected recent examples: a) M. Salavati-Niasari, J. Hasanalian, H. Najafian, J. Mol. Catal. 2004, 209, 209-214;
56. b) V. R. Choudhary, S. K. Jana, V. S. Narkhede, Appl. Catal. A 2002, 235, 207-215;
57. c) V. R. Choudhary, S. K. Jana, J. Mol. Catal. A 2002, 180, 267-276;
58. d) X. Hu, G. K. Chuah, S. Jaenicke, Appl. Catal. A 2001, 277, 1-2;
59. e) V. R. Choudhary, S. K. Jana, J. Catal. 2001, 201, 225-235;
60. f) A. B. Deshpande, A. R. Bajpai, S. D. Samant, Appl. Catal. A 2001, 209, 229-235.
61. A special exception is the cyclization of substituted benzyl alcohols with pyrrole see: a) G. Dyker, D. Hildebrandt, J. Liu, K. Merz, Angew. Chem. 2003, 115, 4536-4538; Angew. Chem. Int. Ed. 2003. 42, 4399-4402;
62. A special exception is the cyclization of substituted benzyl alcohols with pyrrole see: a) G. Dyker, D. Hildebrandt, J. Liu, K. Merz, Angew. Chem. 2003, 115, 4536-4538; Angew. Chem. Int. Ed. 2003. 42, 4399-4402;
63. see also: b) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S. Uemura, Angew. Chem. 2003, 775, 2663-2666; Angew. Chem. Int. Ed. 2003, 42, 2681-2684;
64. see also: b) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai, S. Uemura, Angew. Chem. 2003, 775, 2663-2666; Angew. Chem. Int. Ed. 2003, 42, 2681-2684;
65. c) Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura, Angew. Chem. 2003, 225, 1533-1536; Angew. Chem. Int. Ed. 2003, 42, 1495-1498.
66. c) Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura, Angew. Chem. 2003, 225, 1533-1536; Angew. Chem. Int. Ed. 2003, 42, 1495-1498.
67. E. Mincione, P. Bovicelli, Gazz. Chim. Ital. 1982, 112, 437-440.
68. a) T. Kondo, S. Kajiya, S. Tantayanon, Y. Watanabe, J. Organomet. Chem. 1995, 489, 83-91;
69. b) T. Kondo, S. Tantayanon, Y. Tsuji, Y. Watanabe, Tetrahedron Lett. 1989, 30, 4137-4140.
70. 6] was used, the yield of 1 was 81% (43%).
71. 6] at 80 °C afforded 97% (42%) yield of 4-chloro-1-methoxy-2-(1-phenylethyl)benzene.