PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2012 | 10 | 4 | 1059-1065
Article title

Preparation of a series of N-alkyl-3-boronopyridinium halides and study of their stability in the presence of hydrogen peroxide

Content
Title variants
Languages of publication
EN
Abstracts
EN
A simple and efficient protocol for the preparation of a series of N-alkyl-3-boronopyridinium salts is described which requires exposure of 3-pyridineboronic acid neopentylglycol ester and corresponding alkyle halide to microwave irradiation followed by boronic ester hydrolysis. The technique employed drastically reduces the reaction time and prevents thermal degradation and the formation of side products. Water solutions of the obtained boronopyridinium salts are shown to be stable at room temperature in wide pH range as well as in the presence of hydrogen peroxide at pH 10.0 for 72 h. [...]
Publisher
Journal
Year
Volume
10
Issue
4
Pages
1059-1065
Physical description
Dates
published
1 - 8 - 2012
online
29 - 5 - 2012
References
  • [1] D.G. Hall (Ed.), Boronic Acids. Preparation and Applications in Organic Synthesis and Medicine (Wiley-VCH, Weinheim, 2005) 549 [WoS]
  • [2] P.N. Craig, In: C.J. Drayton (Ed.), Comprehensive Medicinal Chemistry (Pergamon Press, New York, 1991) Vol. 8
  • [3] A.L. Korich, P.M. Iovine. Dalton Trans. 39, 1423 (2010) http://dx.doi.org/10.1039/b917043j[Crossref]
  • [4] N. Fujita, S. Shinkai, T.D. James. Chem. Asian J. 3, 1076 (2008) http://dx.doi.org/10.1002/asia.200800069[Crossref]
  • [5] T.D. James, M.D. Phillips, S. Shinkai, Boronic Acids in Saccharide Recognition (RSC Publishing, Cambridge, 2006)
  • [6] T. Maki, S. Ishihara, H. Yamamoto, Org. Lett. 7(22), 5047 (2005) http://dx.doi.org/10.1021/ol052061d[Crossref]
  • [7] T. Maki, S. Ishihara, H. Yamamoto, Tetrahedron 63, 8645 (2007) http://dx.doi.org/10.1016/j.tet.2007.03.157[Crossref]
  • [8] D.M. Davies, M.E. Deary, K. Quill, R.A. Smith, Chem. Eur. J. 11(12), 3552 (2005) http://dx.doi.org/10.1002/chem.200401209[Crossref]
  • [9] C.A. Bunton, H.J. Foroudian, A. Kumar. J. Chem. Soc. Perkin Trans. 2, 33, (1995) http://dx.doi.org/10.1039/p29950000033[Crossref]
  • [10] H. Matondo, J.C. Garrigues, I. Rico-Lattes, A. Lattes, Appl. Organometal. Chem. 23, 191 (2009) http://dx.doi.org/10.1002/aoc.1493[Crossref]
  • [11] A.F. Popov. Pure Appl. Chem. 80, 1381 (2008) http://dx.doi.org/10.1351/pac200880071381[Crossref]
  • [12] O. Savsunenko et al., J. Surfact. Deterg., DOI: 10.1007/s11743-011-1315-y [Crossref]
  • [13] L.K. Mohler, A.W. Czarnik, J. Am. Chem. Soc. 115, 2998 (1993) http://dx.doi.org/10.1021/ja00060a067[Crossref]
  • [14] R.S. Varma, V.V. Namboodiri, Pure Appl. Chem. 73(8), 1309 (2001) http://dx.doi.org/10.1351/pac200173081309[Crossref]
  • [15] C.O. Kappe, Angew. Chem., Int. Ed. 43, 6250 (2004) http://dx.doi.org/10.1002/anie.200400655[Crossref]
  • [16] D. Dallinger, H. Lehmann, J.D. Moseley, A. Stadler, C.O. Kappe, Org. Process Res. Dev. 15(4), 841 (2011) [Crossref]
  • [17] J.T. Tierney, P. Lindström (Eds.), Microwave-assisted Organic Synthesis (Blackwell, Oxford, 2005) http://dx.doi.org/10.1002/9781444305548[Crossref]
  • [18] N.E. Leadbeater, Microwave heating as a tool for sustainable chemistry (CRC Press, Boca Raton, 2011) 278
  • [19] G.W.V. Cave, C.L. Raston, J.I. Scott, Chem. Commun. 2159 (2001) [Crossref]
  • [20] S. Chatti, M. Bortolussi, A. Loupy, Tetrahedron, 57, 4365 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00318-0[Crossref]
  • [21] H.P. Nguyen, H. Matondo, M. Baboulene, Green Chem. 5, 303 (2003) http://dx.doi.org/10.1039/b303892k[Crossref]
  • [22] J. Kua, M.N. Fletcher, P.M. Iovine, J. Phys. Chem. A 110, 8158 (2006) http://dx.doi.org/10.1021/jp062055e[Crossref]
  • [23] J.C. Peprin, R.N. Keller. J. Am. Chem. Soc. 80, 182 (1958) http://dx.doi.org/10.1021/ja01534a046[Crossref]
  • [24] M. Deetflets, K.R. Seddon, Green Chem. 5, 181 (2003) http://dx.doi.org/10.1039/b300071k[Crossref]
  • [25] R.N. Gedye, F.E. Smith, K.C. Wetaway, Can. J. Chem. 66, 17 (1988) http://dx.doi.org/10.1139/v88-003[Crossref]
  • [26] H. Kuivila. J. Am. Chem. Soc. 76, 870 (1954) http://dx.doi.org/10.1021/ja01632a070[Crossref]
  • [27] R. Glaser, N. Knotts J. Phys. Chem. A 110, 1295 (2006) http://dx.doi.org/10.1021/jp053658d[Crossref]
  • [28] F.C. Fisher, E. Havinga, Recl. Trav. Chim. Pays-Bas 93, 21 (1974) http://dx.doi.org/10.1002/recl.19740930110[Crossref]
  • [29] D.E. Richardson, H. Yao, K.M. Frank, D.A. Bennett, J. Am. Chem. Soc. 122, 1729 (2000) http://dx.doi.org/10.1021/ja9927467[Crossref]
  • [30] Y. Kono, K. Ishira, A. Nagasawa, K. Umemoto, K. Saito, Inorg. Chim. Acta 262, 91 (1997) http://dx.doi.org/10.1016/S0020-1693(97)05499-6[Crossref]
  • [31] R. Pizer, Ch. Tihal. Inorg. Chem. 26(21), 3639 (1987) http://dx.doi.org/10.1021/ic00268a046[Crossref]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0006-5
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.