Synthesis of corrole derivatives through regioselective Ir-catalyzed direct borylation

Angewandte Chemie - International Edition

Volumn 44, Issue 41, 2005, Pages 6763-6766

  Hiroto, Satoru ^a,b   Hisaki, Ichiro ^a,b   Shinokubo, Hiroshi ^a,b   Osuka, Atsuhiro ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Boron; Corroles; Cross coupling; Iridium; Porphyrinoids

Indexed keywords

C-H ACTIVATION; CORROLES; IRIDIUM CATALYSIS; PORPHYRINOIDS;

ACTIVATION ANALYSIS; BORON; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; IRIDIUM COMPOUNDS; PORPHYRINS;

SYNTHESIS (CHEMICAL);

BORON DERIVATIVE; CORROLE; IRIDIUM; ORGANOMETALLIC COMPOUND; PORPHYRIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STANDARD; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BORON COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; IRIDIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PORPHYRINS; REFERENCE STANDARDS; STEREOISOMERISM;

EID: 27444432329     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502335     Document Type: Article

References (41)

1. For excellent reviews on corroies, see: a) (synthesis) D. T. Gryko, Eur. J. Org. Chem. 2002, 1735;
2. b) (oxidation catalysis) Z. Gross, H. B. Gray, Adv. Synth. Catal. 2004, 346, 165;
3. c) (electronic properties) A. Ghosh, E. Steene, J. Inorg. Biochem. 2002, 91, 423.
4. a) D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2001, 34, 40;
5. b) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
6. c) M. G. H. Vicente, L. Jaquinod, K. M. Smith, Chem. Commun. 1999, 1771;
7. d) H. L. Anderson, Chem. Commun. 1999, 2323;
8. e) D. Holten, D. F. Bocian, J. S. Lindsey, Acc. Chem. Res. 2002, 35, 57;
9. f) D. Kim, A. Osuka, Acc. Chem. Res. 2004, 37, 735;
10. g) J.-H. Chou, M. E. Kosal, N. H. Nalwa, S. A. Rakow, K. S. Suslick in The Porphyrin Handbook, Vol. 6 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, New York, 1999, p. 43.
11. a) K. M. Kadish, Z. Ou, J. Shao, C. P. Gros, J.-M. Barbe, F. Jérôme, F. Bolze, F. Burdet, R. Guilard, Inorg. Chem. 2002, 41, 3990;
12. b) R. Guilard, F. Jérôme, J.-M. Barbe, C. P. Gros, Z. Ou, J. Shao, J. Fischer, R. Weiss, K. M. Kadish, Inorg. Chem. 2000, 39, 4856;
13. c) R. Paolesse, R. K. Pandey, T. P. Forsyth, L. Jaquinod, K. R. Gerzevske, D. J. Nurco, M. O. Senge, S. Licoccia, T. Boschi, K. M. Smith, J. Am. Chem. Soc. 1996, 118, 3869.
14. a) R. Paolesse, S. Nardis, F. Sagone, R. G. Khoury, J. Org. Chem. 2001, 66, 550;
15. b) G. Golubkov, J. Bendix, H. B. Gray, A. Mahammed, I. Goldberg, A. J. DiBilio, Z. Gross, Angew. Chem. 2001, 113, 2190;
16. Angew. Chem. Int. Ed. 2001, 40, 2132;
17. c) A. Mahammed, I. Goldberg, Z. Gross, Org. Lett. 2001, 3, 3443;
18. d) I. Saltsman, A. Mahammed, I. Goldberg, E. Tkachenko, M. Botoshansky, Z. Gross, J. Am. Chem. Soc. 2002, 124, 7411;
19. e) R. Paolesse, S. Nardis, M. Venanzi, M. Mastroianni, M. Russo, F. R. Fronczek, M. G. H. Vicente, Chem. Eur. J. 2003, 9, 1192.
20. H. Hata, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2005, 127, 8264.
21. For Ir-catalyzed direct borylations of aromatic compounds, see: T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2003, 680, 3;
22. a) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr., M. R. Smith III, Science 2002, 295, 305, and references therein;
23. b) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390, and references therein.
24. a) D. T. Gryko, B. Koszarna, Org. Biomol. Chem. 2003, 1, 350;
25. b) Z. Gross, N. Galili, I. Saltsman, Angew. Chem. 1999, 111, 1530;
26. Angew. Chem. Int. Ed. 1999, 38, 1427;
27. c) J. P. Collman, R. A. Decreau, Tetrahedron Lett. 2003, 44, 1207.
28. -3, Z = 4. For 30529 reflections measured; R = 0.096, wR (all data) = 0.1616, GOF = 1.099 [I>2σ(I)]. CCDC-276228 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
29. a) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399;
30. b) M. O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165;
31. c) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057;
32. d) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93;
33. Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
34. e) N. Aratani, A. Osuka, Y. H. Kim, D. H. Jeong, D. Kim, Angew. Chem. 2000, 112, 1517;
35. Angew. Chem. Int. Ed. 2000, 39, 1458.
36. A cobalt complex of a directly linked dicorrole has been synthesized; see: A. Mahammed, I. Giladi, I. Goldberg, Z. Gross, Chem. Eur. J. 2001, 7, 4259.
37. R. E. Maleczka, Jr., F. Shi, D. Holmes, M. R. Smith III, J. Am. Chem. Soc. 2003, 125, 7792.
38. For the isolation of other types of dihydrocorroles, see: A. Mahammed, Z. Gross, J. Inorg. Biochem. 2002, 898, 305.
39. For the tautomerization of 2-hydroxyporphyrins, see: M. J. Crossley, M. M. Harding, S. Sternhell, J. Org. Chem. 1988, 53, 1132.
40. a) T. Ding, J. D. Harvey, C. J. Ziegler, J. Porphyrins Phthalocyanines 2005, 9, 22;
41. b) Y. S. Balazs, I. Saltsman, A. Mahammed, E. Tkachenko, G. Golubkov, J. Levine, Z. Gross, Magn. Reson. Chem. 2004, 42, 624.