5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly reactive and recoverable organo-bismuth reagents for cross-coupling reactions with Aryl Bromides

Angewandte Chemie - International Edition

Volumn 42, Issue 16, 2003, Pages 1845-1848

  Shimada, Shigeru ^a   Yamazaki, Osamu ^a   Tanaka, Toshifumi ^b   Rao, Maddali L N ^a   Suzuki, Yohichi ^b   Tanaka, Masato ^a,c  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Bismuth boron; Cross coupling; Hypervalent compounds; Palladium

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; CHEMICAL REACTIONS; ESTERS;

MULTI-COUPLING REACTIONS;

BISMUTH COMPOUNDS;

5,6,7,12 TETRAHYDRODIBENZ[C,F][1,5]AZABISMOCINE; BISMUTH DERIVATIVE; ORGANIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MOLECULAR DYNAMICS; REACTION ANALYSIS; SYNTHESIS;

EID: 0038031649     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250205     Document Type: Article

References (39)

1. a) Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998;
2. b) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
3. b) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701; Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
4. c) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469.
5. For recent examples, see: a) V. P. W. Bohm, C. W. K. Gstottmayr, T. Weskamp, W.A. Herrmann, Angew. Chem. 2001, 113, 3500-3503; Angew. Chem. Int. Ed. 2001, 40, 3387-3389;
6. For recent examples, see: a) V. P. W. Bohm, C. W. K. Gstottmayr, T. Weskamp, W.A. Herrmann, Angew. Chem. 2001, 113, 3500-3503; Angew. Chem. Int. Ed. 2001, 40, 3387-3389;
7. b) C. Y. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719-2724;
8. c) S. E. Denmark, R. F. Sweis, J. Am. Chem. Soc. 2001, 123, 6439-6440;
9. d) K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 11577-11585;
10. e) A. Mori, M. Suguro, Synlett 2001, 845-847;
11. f) A. Ftirstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
12. f) A. Ftirstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
13. g) J. J. Yin, M. P. Rainka, X. X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162-1163;
14. h) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423; Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
15. h) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423; Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
16. a) I. Perez, J. P. Sestelo, L. A. Sarandeses, Org. Lett. 1999, 1, 1267-1269;
17. b) I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155-4160.
18. a) E. Riguet, M. Alami, G. Cahiez, Tetrahedron Lett. 1997, 38, 4397-4400;
19. b) E. Riguet, M. Alami, G. Cahiez, J. Organomet. Chem. 2001, 624, 376-379.
20. J. W Han, N. Tokunaga, T. Hayashi, Synlett 2002, 871-874.
21. a) S. Maeda in The Chemistry of Organic Arsenic, Antimony and Bismuth Compounds (Ed.: S. Patai), Wiley, New York, 1994, chap. 19, pp. 725-759;
22. b) J. Reglinski, in Chemistry of Arsenic, Antimony and Bismuth (Ed.: N. C. Norman), Blackie Academic and Professional, London, 1998, chap. 8, pp. 403-440.
23. For reviews on the application of organobismuth compounds in organic synthesis, see: a) H. Suzuki, T. Ikegami, Y. Matano, Synthesis 1997, 249-267; b) G. I. Elliott, J. P. Konopelski, Tetrahedron 2001, 57, 5683-5705; c) Organobismuth Chemistry (Eds.: H. Suzuki, Y. Matano), Elsevier, Amsterdam, 2001.
24. For reviews on the application of organobismuth compounds in organic synthesis, see: a) H. Suzuki, T. Ikegami, Y. Matano, Synthesis 1997, 249-267; b) G. I. Elliott, J. P. Konopelski, Tetrahedron 2001, 57, 5683-5705; c) Organobismuth Chemistry (Eds.: H. Suzuki, Y. Matano), Elsevier, Amsterdam, 2001.
25. For reviews on the application of organobismuth compounds in organic synthesis, see: a) H. Suzuki, T. Ikegami, Y. Matano, Synthesis 1997, 249-267; b) G. I. Elliott, J. P. Konopelski, Tetrahedron 2001, 57, 5683-5705; c) Organobismuth Chemistry (Eds.: H. Suzuki, Y. Matano), Elsevier, Amsterdam, 2001.
26. a) M. L. N. Rao, S. Shimada, M. Tanaka, Org. Lett. 1999, 1, 1271-1273;
27. b) M. L. N. Rao, O. Yamazaki, S. Shimada, T. Tanaka, Y. Suzuki, M. Tanaka, Org. Lett. 2001, 3, 4103-4105;
28. c) M. L. N. Rao, S. Shimada, O. Yamazaki, M. Tanaka, J. Organomet. Chem. 2002, 659, 117-120.
29. a) K. Ohkata, S. Takemoto, M. Ohnishi, K. Akiba, Tetrahedron Lett. 1989, 30, 4841-4844;
30. b) M. Minoura, Y. Kanamori, A. Miyake, K. Akiba, Chem. Lett. 1999, 861-862.
31. F. H. Carré, R. J. P. Corriu, G. F. Lanneau, P. Merle, F. Soulairol, J. Yao, Organometallics 1997, 16, 3878-3888.
32. Compounds 3a-3g were purified by recrystallization and are thermally stable at least up to 110°C. Compounds 3a, 3 b, 3 f, and 3g also can be purified by silica-gel column chromatography, whereas 3 d seems to decompose by column chromatography on silica gel or alumina. Detail of the synthesis, structure, and some properties of 3 a-3 g will be reported elsewhere.
33. 3 as observed in the related cross-coupling reaction; see: B. E. Segelstein, T. W. Butler, B. L. Chenard, J. Org. Chem. 1995, 60, 12-13.
34. 2/4M aqueous HCl at room temperature for 2 days.
35. For an experimental procedure, see Supporting Information.
36. A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
37. 2Br were also formed.
38. Similar compounds have been prepared by multistep procedures: T. M. Miller, T. X. Neenan, R. Zayas, H. E. Bair, J. Am. Chem. Soc. 1992, 114, 1018-1025.
39. The molecular structure of 7a was unambiguously confirmed by X-ray analysis. See the Supporting Information for the crystal data as well as a molecular drawing of 7a. CCDC-192709 (7a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.-ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.cam.ac.uk).