Boronate linker for 'traceless' solid-phase synthesis

Chemical Communications

Volumn , Issue 14, 2000, Pages 1275-1276

  Pourbaix, Christelle ^a   Carreaux, François ^a   Carboni, Bertrand ^a   Deleuze, Hervé ^b  

^a Chimie et Photonique Moleculaires Rennes   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BORONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; SOLID; SYNTHESIS;

EID: 0034698311     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b003487h     Document Type: Article

References (16)

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2. For selected reviews, see: D. Obrecht and J. M. Villalgordo, Solid Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compounds Libraries, Pergamon, New York, 1998; L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555; B. Jandeleit, D. J. Schaefer, T. S. Power, H. W. Turner and W. H. Weinberg, Angew. Chem., Int. Ed., 1999, 38, 2494.
3. For selected reviews, see: D. Obrecht and J. M. Villalgordo, Solid Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compounds Libraries, Pergamon, New York, 1998; L. A. Thompson and J. A. Ellman, Chem. Rev., 1996, 96, 555; B. Jandeleit, D. J. Schaefer, T. S. Power, H. W. Turner and W. H. Weinberg, Angew. Chem., Int. Ed., 1999, 38, 2494.
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5. B. Carboni, C. Pourbaix, F. Carreaux, H. Deleuze and B. Maillard, Tetrahedron Lett., 1999, 40, 7979.
6. For other preparations of resin bound boronic acids, see: D. G. Hall, J. Taylor and M. Gravel, Angew. Chem., Int. Ed., 1999, 38, 3064; W. Li and K. Burgess, Tetrahedron Lett., 1999, 40, 6527.
7. For other preparations of resin bound boronic acids, see: D. G. Hall, J. Taylor and M. Gravel, Angew. Chem., Int. Ed., 1999, 38, 3064; W. Li and K. Burgess, Tetrahedron Lett., 1999, 40, 6527.
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13. The glycerol-PS resin (Purchased from Novabiochem. Inc.) was coupled to m-nitrophenylboronic acid in THF, under the same conditions as with resin 1.
14. A small amount of boronic acid can be detected in some cases, (5-10%). This by-product results from the hydrolysis of the boronate linker and is easily removed by treating the crude of the reaction after cleavage with the diol resin 1 under the immobilization conditions of boronic acids. The polymer 1 is then used as solid-supported scavenger of boronic acids.
15. I. Ugi, S. Lohberger and R. Karl, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon, New York, 1991, Vol. 2, p. 1083.
16. All new, nonpolymeric compounds were completely characterized (1H NMR, 13C NMR, IR, MS, elemental analysis, or HRMS).