Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid in Liquid Tetrabutylammonium Bromide

Yangyang Liu; Aming Xie; Meiping Cao; Liandong Feng; Boliang Wang

doi:10.14233/ajchem.2015.17046

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid in Liquid Tetrabutylammonium Bromide

https://doi.org/10.14233/ajchem.2015.17046

Yangyang Liu

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P.R. China

Aming Xie

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P.R. China

Meiping Cao

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P.R. China

Liandong Feng

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P.R. China

Boliang Wang

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P.R. China

Corresponding Author(s) : Boliang Wang

boliangwang@njust.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

A mild, green and low cost method for o-iodoxybenzoic acid mediated oxidation of alcohols to carbonyl compounds has been established. In this protocol, liquid tetrabutylammonium bromide was used as the solvent and the primary alcohols were selectively oxidized to aldehyde and secondary alcohols were easily transformed to ketones.

Keywords

o-Iodoxybenzoic acid Oxidation Tetrabutylammonium bromide

Liu, Y., Xie, A., Cao, M., Feng, L., & Wang, B. (2015). Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid in Liquid Tetrabutylammonium Bromide. Asian Journal of Chemistry, 27(2), 587–590. https://doi.org/10.14233/ajchem.2015.17046

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References

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References

K. Mori, T. Hara, T. Mizugaki, K. Ebitani and K. Kaneda, J. Am. Chem. Soc., 126, 10657 (2004); doi:10.1021/ja0488683.

K. Bowden, I.M. Heilbron, E.R.H. Jones and B.C.L. Weedon, J. Chem. Soc., 39 (1946); doi:10.1039/jr9460000039.

E.J. Corey and J.W. Suggs, Tetrahedron Lett., 16, 2647 (1975); doi:10.1016/S0040-4039(00)75204-X.

E.J. Corey and C.U. Kim, J. Am. Chem. Soc., 94, 7586 (1972); doi:10.1021/ja00776a056.

H. Tomioka, K. Takai, K. Oshima and H. Nozaki, Tetrahedron Lett., 22, 1605 (1981); doi:10.1016/S0040-4039(01)90389-2.

I.E. Markó, P.R. Giles, M. Tsukazaki, S.M. Brown and C.J. Urch, Science, 274, 2044 (1996); doi:10.1126/science.274.5295.2044.

T. Mallat and A. Baiker, Chem. Rev., 104, 3037 (2004); doi:10.1021/cr0200116.

R. Liu, X. Liang, C. Dong and X. Hu, J. Am. Chem. Soc., 126, 4112 (2004); doi:10.1021/ja031765k.

B. Karimi, A. Biglari, J.H. Clark and V. Budarin, Angew. Chem. Int. Ed., 46, 7210 (2007); doi:10.1002/anie.200701918.

X. Wang, R. Liu, Y. Jin and X. Liang, Chem. Eur. J., 14, 2679 (2008); doi:10.1002/chem.200701818.

Y. Xie, W. Mo, D. Xu, Z. Shen, N. Sun, B. Hu and X. Hu, J. Org. Chem., 72, 4288 (2007); doi:10.1021/jo0705824.

M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa and Y. Iwabuchi, J. Am. Chem. Soc., 133, 6497 (2011); doi:10.1021/ja110940c.

K.C. Nicolaou, P.S. Baran, Y. Zhong, S. Barluenga, K.W. Hunt, R. Kranich and J.A. Vega, J. Am. Chem. Soc., 124, 2233 (2002); doi:10.1021/ja012126h.

K.C. Nicolaou, T. Montagnon, P.S. Baran and Y. Zhong, J. Am. Chem. Soc., 124, 2245 (2002); doi:10.1021/ja012127+.

K.C. Nicolaou, C.J.N. Mathison and T. Montagnon, J. Am. Chem. Soc., 126, 5192 (2004); doi:10.1021/ja0400382.

A. Duschek and S.F. Kirsch, Angew. Chem. Int. Ed., 50, 1524 (2011); doi:10.1002/anie.201000873.

A.P. Thottumkara and T.K. Vinod, Tetrahedron Lett., 43, 569 (2002); doi:10.1016/S0040-4039(01)02217-1.

Z. Liu, Z. Chen and Q. Zheng, Org. Lett., 5, 3321 (2003); doi:10.1021/ol0351549.

A.P. Thottumkara, M.S. Bowsher and T.K. Vinod, Org. Lett., 7, 2933 (2005); doi:10.1021/ol050875o.

A. Schulze and A. Giannis, Synthesis, 257 (2006); doi:10.1055/s-2005-924764.

B.C. Ranu, A. Das and S. Samanta, J. Chem. Soc., Perkin Trans. 1, 1520 (2002); doi:10.1039/b204363g.

B.C. Ranu and S.S. Dey, Tetrahedron Lett., 44, 2865 (2003); doi:10.1016/S0040-4039(03)00439-8.

I. González, S. Bouquillon, A. Roglans and J. Muzart, Tetrahedron Lett., 48, 6425 (2007); doi:10.1016/j.tetlet.2007.07.073.

A. Xie, M. Cao, L. Feng and W. Dong, J. Chem. Res., 37, 665 (2013); doi:10.3184/174751913X13812404042931.

C. Miao, L. He, J. Wang and F. Wu, J. Org. Chem., 75, 257 (2010); doi:10.1021/jo902292t.

R. Chorghade, C. Battilocchio, J.M. Hawkins and S.V. Ley, Org. Lett., 15, 5698 (2013); doi:10.1021/ol4027107.

G. Zhang and S.K. Hanson, Org. Lett., 15, 605 (2013).

R. Kawahara, K.- Fujita and R. Yamaguchi, J. Am. Chem. Soc., 134, 3643 (2012); doi:10.1021/ja210857z.

S. Korsager, R.H. Taaning, A.T. Lindhardt and T. Skrydstrup, J. Org. Chem., 78, 6112 (2013); doi:10.1021/jo400741t.

J.E. Steves and S.S. Stahl, J. Am. Chem. Soc., 135, 15742 (2013); doi:10.1021/ja409241h.

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid in Liquid Tetrabutylammonium Bromide

Corresponding Author(s) : Boliang Wang

Abstract

Keywords

Full Article

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