Synthesis and characterization of 2,6-difluoro-4-carboxyphenylboronic acid and a biotin derivative thereof as captors of anionic aqueous [18F]-fluoride for the preparation of [18F/19F]-labeled aryltrifluoroborates with high kinetic stability

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3152-3156

  Harwig, Curtis W ^a   Ting, Richard ^a   Adam, Michael J ^a,b   Ruth, Thomas J ^b   Perrin, David M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b TRIUMF   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN DERIVATIVE; BORIC ACID; BORONIC ACID DERIVATIVE; FLUORINE; FLUORINE 18; TRIFLUOROBORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEFLUORIDATION; ISOTOPE LABELING; KINETICS; PH MEASUREMENT; POSITRON EMISSION TOMOGRAPHY; SOLVOLYSIS; THERMODYNAMICS; THIN LAYER CHROMATOGRAPHY;

EID: 41649088782     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.021     Document Type: Article

References (20)

1. For an excellent overview of this field, see:. In: Hall D.G. (Ed). Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. 1st ed. (2005), Wiley-VCH, Weinheim
2. Ting R., Adam M.J., Ruth T.J., and Perrin D.M. J. Am. Chem. Soc. 127 (2005) 13094-13095
3. Ting R.; Lo J.; Adam M. J.; Ruth T. J.; Perrin D. M., J. Fluorine Chem., in press, doi:10.1016/j.jfluchem.2008.01.011.
4. Ting, R.; Harwig, C.; Lo, J.; Li, Y.; Adam, M. J.; Ruth, T. J.; Perrin, D. M. Manuscript in preparation.
5. For related examples of this type of regioselectivity, see:. Demas M., Javadi G.J., Bradley L.M., and Hunt D.A. J. Org. Chem. 65 (2000) 7201-7202
6. - (dimethylboronate ester) 229.0484, found 229.0477.
7. - 283.0953, found 283.0947.
8. Konoki K., Sugiyama N., Murata M., Tachibana K., and Hatanaka Y. Tetrahedron 56 (2000) 9003-9014
9. 19F NMR of deboronated adduct 7 consists of a peak at -31.9 ppm whereas, in the desired boronate ester 6, the 2,6-difluoro groups appear as a peak considerably downfield at -22.8 ppm.
10. Gravel M., Thompson K.A., Zak M., Berube C., and Hall D.G. J. Org. Chem. 67 (2002) 3-15
11. 19F NMR, indicating a ∼1:1 mixture of 1:2.
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15. For a discussion of protolytic deboronation, see:. Hall D.G., and Suzuki A. In: Hall D.G. (Ed). Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. 1st ed. (2005), Wiley-VCH, Weinheim 14 143
16. Review:. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2470
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18. + 617.2756, found 617.2736.
19. - 531.1579, found 531.1594.
20. + 865.3382, found 865.3374.