Synthesis of amine-borane intramolecular complexes through palladium-catalyzed rearrangement of Ammonioalkynyltriarylborates

Organic Letters

Volumn 10, Issue 6, 2008, Pages 1279-1281

  Ishida, Naoki ^a   Narumi, Mizuna ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149147001     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8001305     Document Type: Article

References (23)

1. Reviews: (a) Entwistle, C. D.; Marder, T. B. Chem. Mater. 2004, 16, 4574.
2. (b) Yamaguchi, S.; Wakamiya, A. Pure Appl. Chem. 2006, 78, 1413.
3. (c) Jäkle, F. Coord. Chem. Rev. 2006, 250, 1107.
4. (a) Wakamiya, A.; Taniguchi, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2006, 45, 3170.
5. (b) Yoshino, J.; Kano, N.; Kawashima, T. Chem. Commun. 2007, 559.
6. (c) Jaska, C. A.; Piers, W. E.; McDonald, R.; Parvez, M. J. Org. Chem. 2007, 72, 5234.
7. Ishida, N.; Miura, T.; Murakami, M. Chem. Commun. 2007, 4381. For related migration reactions of alkynyltriorganylborates, see references therein.
8. The alkynylborate la was prepared in 83% yield by the reaction of the corresponding lithium acetylide with triphenylborane-pyridine complex followed by treatment with pyridinium chloride.
9. (a) Miyaura, N.; Yoshinari, T.; Itoh, M.; Suzuki, A. Tetrahedron Lett. 1974, 15, 2961.
10. (b) Pelter, A.; Harrison, C. R.; Subrahmanyam, C.; Kirkpatrick, D. J. Chem. Soc, Perkin Trans. I 1976, 2435.
11. For previous examples of generation of palladium(II) hydride species by protonation of Pd(0) and a subsequent hydropalladation process, see:
12. (a) Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828.
13. (b) Grushin, V. V. Chem. Rev 1996, 96, 2011.
14. (c) Zargarian, D.; Alper, H. Organometallics 1993, 12, 712.
15. (d) Tani, K.; Ono, N.; Okamoto, S.; Sato, F. J. Chem. Soc, Chem. Commun 1993, 386.
16. (e) Trost, B. M.; Braslau, R. Tetrahedron Lett. 1989, 30, 4657.
17. For examples of simple hydroarylation reactions catalyzed by palladium, see:
18. (a) Trost, B. M.; Toste, F. D.; Greenman, K. J. Am. Chem. Soc. 2003, 125, 4518.
19. (b) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
20. These values were determined in Me OH solutions. Williams, J. L. R.; Webster, S. K.; Van Allan, J. A. J. Org. Chem. 1961, 26, 4893.
21. Pyridine ring was preferentially borylated over phenyl C-H bonds.
22. (a) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649.
23. (b) 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.