-
PDF
- Split View
-
Views
-
Cite
Cite
Shunpei Hitosugi, Daiki Tanimoto, Waka Nakanishi, Hiroyuki Isobe, A Facile Chromatographic Method for Purification of Pinacol Boronic Esters, Chemistry Letters, Volume 41, Issue 9, September 2012, Pages 972–973, https://doi.org/10.1246/cl.2012.972
Close - Share Icon Share
Abstract
A facile chromatographic method for purification of pinacol boronic esters has been developed. Impregnation of silica gel with boric acid was effective both for thin layer chromatography (TLC) and for flash column chromatography. Purification of a series of pinacol boronic esters was successful by suppressing loss of the compounds due to over-adsorption.
References
W. A. Scrivens, P. V. Bedworth, J. M. Tour, J. Am. Chem. Soc. 1992, 114, 7917;
W. A. Scrivens, A. M. Cassell, B. L. North, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 6939;
K. Nagata, E. Dejima, Y. Kikuchi, M. Hashiguchi, Chem. Lett. 2005, 34, 178.
P. K. Ruprah, J.-P. Cros, J. E. Pease, W. G. Whittingham, J. M. J. Williams, Eur. J. Org. Chem. 2002, 3145.
H. Isobe, T. Tanaka, R. Maeda, E. Noiri, N. Solin, M. Yudasaka, S. Iijima, E. Nakamura, Angew. Chem., Int. Ed. 2006, 45, 6676;
S. Hitosugi, W. Nakanishi, T. Yamasaki, H. Isobe, Nat. Commun. 2011, 2, Article number 492;
H. Isobe, S. Hitosugi, T. Matsuno, T. Iwamoto, J. Ichikawa, Org. Lett. 2009, 11, 4026;
S. Hitosugi, Y. Nakamura, T. Matsuno, W. Nakanishi, H. Isobe, Tetrahedron Lett. 2012, 53, 1180.
Cross-Coupling Reactions: A Practical Guide in Topics in Current Chemistry, ed. by N. Miyaura, Springer-Verlag, Berlin, 2002, Vol. 219. doi:10.1007/3-540-45313-X;
L. Gao, M. A. Peay, D. V. Partyka, J. B. Updegraff, III, T. S. Teets, A. J. Esswein, M. Zeller, A. D. Hunter, T. G. Gray, Organometallics 2009, 28, 5669.
R. K. Iler, The Chemistry of Silica: Solubility, Polymerization, Colloid and Surface Properties, and Biochemistry, Wiley, New York, 1979;
W. S. Rasband, U. S. National Institutes of Health, Bethesda, Maryland, USA, http://imagej.nih.gov/ij/, 1997–2012.
H. Isobe, N. Tomita, J. W. Lee, H.-J. Kim, K. Kim, E. Nakamura, Angew. Chem., Int. Ed. 2000, 39, 4257;
H. Isobe, S. Sugiyama, K.-i. Fukui, Y. Iwasawa, E. Nakamura, Angew. Chem., Int. Ed. 2001, 40, 3364.