Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines

Journal of the American Chemical Society

Volumn 131, Issue 17, 2009, Pages 6070-6071

  Ohmura, Toshimichi ^a   Kijima, Akihito ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORYLATION; CROSS-COUPLED; HIGH YIELD; IODOBENZENE; ISOINDOLES; PALLADIUM-CATALYZED REACTIONS; PINACOLBORANE; SELECTIVE FORMATION;

SYNTHESIS (CHEMICAL);

PALLADIUM;

1 BORYLISOINDOLE; ISOINDOLE DERIVATIVE; PALLADIUM; TOLUENE; UNCLASSIFIED DRUG; BORON DERIVATIVE; INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CATALYST; DEHYDROGENATION; HYDROGENATION; SUBSTITUTION REACTION; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; HYDROGENATION; INDOLES; ISOINDOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 70149112780     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja901095h     Document Type: Article

References (35)

1. (a) Tyrrell, E.; Brookes, P. Synthesis 2004, 469.
2. (b) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
3. (c) Palladium in Heterocyclic Chemistry, 2nd ed.; Li, J. J., Gribble, G. W., Eds.; Elsevier: Oxford, 2007.
4. (a) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
5. (b) Ishiyama, T.; Miyaura, N. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 101.
6. (a) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
7. (b) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997, 62, 6458.
8. (c) Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813.
9. Examples of C-H borylation of heterocyclic compounds: (a) Tse, M. K.; Cho, J.-Y.; Smith, M. R., III. Org. Lett. 2001, 3, 2831.
10. (b) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
11. (c) Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056.
12. (d) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649.
13. (e) Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. Chem. Commun. 2003, 2924.
14. (f) Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, J. F.; Miyaura, N. Adv. Synth. Catal. 2003, 345, 1103.
15. (g) Mkhalid, I. A. I.; Coventry, D. N.; Albesa-Jove, D.; Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew. Chem., Int. Ed. 2006, 45, 489.
16. (h) Paul, S.; Chotana, G. A.; Holmes, D.; Reichie, R. C.; Maleczka, R. E., Jr.; Smith, M. R., III. J. Am. Chem. Soc. 2006, 128, 15552.
17. (i) Chotana, G. A.; Kallepalli, V. A.; Maleczka, R. E., Jr.; Smith, M. R., III. Tetrahedron 2008, 64, 6103.
18. (a) Jones, G. B.; Chapman, B. J. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 2, p 1.
19. (b) Donohoe, T. J. In Fused Five-Membered Hetarenes with One Heteroatom; Thomas, E. J., Ed.; Science of Synthesis, Vol. 10; Georg Thieme Verlag: Stuttgart, Germany, 2000; p 653.
20. Selected examples of applications. Synthetic intermediate of tetracene: (a) LeHoullier, C. S.; Gribble, G. W. J. Org. Chem. 1983, 48, 2364.
21. (b) Chen, Z.; Müller, P.; Swager, T. M. Org. Lett. 2006, 8, 273.
22. Fluorescent and electroluminescent materials: (c) Zweig, A.; Metzler, G.; Maurer, A.; Roberts, B. G. J. Am. Chem. Soc. 1967, 89, 4091.
23. (d) Ding, Y.; Hay, A. S. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3293.
24. (e) Mi, B.-X.; Wang, P.-F.; Liu, M.-W.; Kwong, H.-L.; Wong, N.-B.; Lee, C.-S.; Lee, S.-T. Chem. Mater. 2003, 15, 3148.
25. Dyes: (f) Naef, R. Dyes Pigments 1985, 6, 233.
26. For examples, see: (a) Winn, M.; Zaugg, H. E. J. Org. Chem. 1969, 34, 249.
27. (b) Simons, S. S., Jr.; Ammon, H. L.; Doherty, R.; Johnson, D. F. J. Org. Chem. 1981, 46, 4739.
28. (c) Bonnett, R.; North, S. A.; Newton, R. F.; Scopes, D. I. C. Tetrahedron 1983, 39, 1401.
29. Palladium-catalyzed benzylic C-H borylation of toluene derivatives: Ishiyama, T.; Ishida, K.; Takagi, J.; Miyaura, N. Chem. Lett. 2001, 30, 1082.
30. In the absence of either Me2S or 6, the NMR yield of 2d decreased to 76 or 68%, respectively.
31. We observed N-borylation (for the N-H derivative), debenzylation (for the N-Bn derivative), and no reaction (for the N-Ph and N-Ts derivatives).
32. Pd-catalyzed conversion of 2-alkylisoindolines to 2-alkyl-4,5,6,7- tetrahy-droisoindoles under hydrogenation conditions has been reported. See: (a) Hou, D.-R.; Hsieh, Y.-D.; Hsieh, Y.-W. Tetrahedron Lett. 2005, 46, 5927.
33. (b) Hou, D.-R.; Wang, M.-S.; Chung, M.-W.; Hsieh, Y.-D.; Tsai, H.-H. G. J. Org. Chem. 2007, 72, 9231. A mechanism involving oxidative addition of benzylic C-H to Pd(0) has been proposed.
34. See: (c) Tsai, H.-H. G.; Chung, M.-W.; Chou, Y.-K.; Hou, D.-R. J. Phys. Chem. A 2008, 112, 5278.
35. One possibility may be the formation of a heterogeneous hydrogenation catalyst, which is easily poisoned by Me2S. See: Freifelder, M. In Practical Catalytic Hydrogenation; Wiley Interscience: New York, 1971; p 23.