Use of in situ isopropoxide protection in the metal-halogen exchange of arylboronates

Journal of Organic Chemistry

Volumn 72, Issue 17, 2007, Pages 6618-6620

  Jiang, Qin ^a   Ryan, Meagan ^a   Zhichkin, Paul ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; HALOGEN COMPOUNDS; ION EXCHANGE; REACTION KINETICS;

ARYLBORONATES; IN SITU ISOPROPOXIDE PROTECTION; METAL-HALOGEN EXCHANGE;

BORON COMPOUNDS;

BORON DERIVATIVE; BROMINE DERIVATIVE; EPOXIDE; HALOGEN; METAL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 34547942339     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0710329     Document Type: Article

References (20)

1. Santucci, L.; Gilman, H. J. Am. Chem. Soc. 1958, 80, 193.
2. For example, see: (a) Letsinger, R. L.; Remes, N. J. Am. Chem. Soc. 1955, 77, 2489.
3. (b) Letsinger, R. L.; Skoog, I. J. Am. Chem. Soc. 1955, 77, 2491.
4. (c) Brown, H. C.; Cole, T. E.; Srebnik, M. Organometallics 1985, 4, 1788.
5. (d) Brown, H. C.; Srebnik, M.; Cole, T. E. Organometallics 1986, 5, 2300.
6. Baron, O.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 3133.
7. Molander, G. A.; Ellis, N. M. J. Org. Chem. 2006, 71, 7491.
8. (a) Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482.
9. (b) Pereira, S.; Srebnik, M. Tetrahedron Lett. 1996, 37, 3283.
10. Pinacolatoboronates have been prepared via hydrolysis of pinacolatoisopropoxyborate intermediate, for example, see: (a) Hoffmann, R. W.; Metternich, R.; Lanz, J. W. Liebigs Ann. Chem. 1987, 881.
11. (b) Krueger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499.
12. (c) Mohacrishnan, A. K.; Hucke, A.; Lyon, M. A.; Lakshmikantham, M. V.; Cava, M. P. Tetrahedron 1999, 55, 11745.
13. (d) Karsten, M.; Dimichele, L.; Mills, P.; Frantz, D. E.; Nelson, T. D.; Kress, M. H. Synlett 2006, 1948.
14. Combi-Blocks: 1a (cat. no. PN-2629) and 1b (cat. no. PN-2655).
15. For the metalation of dibromobenzenes, see: (a) Gilman, H.; Langham, W.; Moore, F. W. J. Am. Chem. Soc. 1940, 62, 2327.
16. (b) Caron, S.; Nga, M. D. Synlett 2004, 1440 and references cited therein.
17. For the use of triisoporopylborate with the following bases, see: (a) n-BuLi: Yasuda, N.; Huffman, M. A.; Ho, G.-J.; Xavier, L. C.; Yang, C.; Emerson, K. M.; Tsay, F.-R.; Li, Y.; Kress, M. H.; Rieger, D. L.; Karady, S.; Sohar, P.; Abramson, N. L.; DeCamp, A. E.; Mathre, D. J.; Douglas, A. W.; Dolling, U.-H.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1998, 63, 5438.
18. (b) n-BuLi: Li, W.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.; Cai, D.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2002, 67, 5394.
19. (c) LTMP: Kristensen, J.; Lysén, M.; Vedso, P.; Begtrup, M. Org. Lett. 2001, 3, 1435.
20. (d) LDA: Caron, S.; Hawkins, J. M.; J. Org. Chem. 1998, 63, 2054.