TFA-Mediated Alkyne Hydration Reaction to Synthesize Methyl Ketones

Z.W. Chen; M.T. Luo; D.N. Ye

doi:10.14233/ajchem.2014.16481

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

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

TFA-Mediated Alkyne Hydration Reaction to Synthesize Methyl Ketones

https://doi.org/10.14233/ajchem.2014.16481

Z.W. Chen

Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P.R. China

M.T. Luo

Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P.R. China

D.N. Ye

Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000, Jiangxi Province, P.R. China

Corresponding Author(s) : Z.W. Chen

chenzwang@126.com

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 18, 2014

Abstract

Trifluoroacetic acid efficiently promotes the hydration of terminal alkynes without the use of other catalysts to afford a wide variety of methyl ketones in good to excellent yields with perfect regioselectivities. This new procedure offers significant advantages over previous synthetic approaches, including brevity, mild reaction conditions, excellent yields and high functional group tolerance.

Keywords

Hydration Terminal alkyne Methyl ketone Trifluoroacetic acid

Chen, Z., Luo, M., & Ye, D. (2014). TFA-Mediated Alkyne Hydration Reaction to Synthesize Methyl Ketones. Asian Journal of Chemistry, 26(19), 6528–6530. https://doi.org/10.14233/ajchem.2014.16481

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References

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References

F. Alonso, I.P. Beletskaya and M. Yus, Chem. Rev., 104, 3079 (2004); doi:10.1021/cr0201068.

L. Hintermann and A. Labonne, Synthesis, 1121 (2007); doi:10.1055/s-2007-966002.

M. Kutscheroff, Ber. Dtsch. Chem. Ges, 14, 1540 (1881); doi:10.1002/cber.188101401320.

B. Neumann and H. Schneider, Angew. Chem., 33, 189 (1920); doi:10.1002/ange.19200336202.

W.L. Budde and R.E. Dessy, J. Am. Chem. Soc., 85, 3964 (1963); doi:10.1021/ja00907a014.

J. Halpern, B.R. James and A.L.W. Kemp, J. Am. Chem. Soc., 83, 4097 (1961); doi:10.1021/ja01480a036.

M.M.T. Khan, S.B. Halligudi and S. Shukla, J. Mol. Catal., 58, 299 (1990); doi:10.1016/0304-5102(90)85019-E.

B.R. James and G.L. Rempel, J. Am. Chem. Soc., 91, 863 (1969); doi:10.1021/ja01032a012.

R. Casado, M. Contel, M. Laguna, P. Romero and S. Sanz, J. Am. Chem. Soc., 125, 11925 (2003); doi:10.1021/ja036049x.

N. Marion, R.S. Ramón and S.P. Nolan, J. Am. Chem. Soc., 131, 448 (2009); doi:10.1021/ja809403e.

D. Wang, R. Cai, S. Sharma, J. Jirak, S.K. Thummanapelli, N.G. Akhmedov, H. Zhang, X. Liu, J.L. Petersen and X. Shi, J. Am. Chem. Soc., 134, 9012 (2012); doi:10.1021/ja303862z.

E. Mizushima, K. Sato, T. Hayashi and M. Tanaka, Angew. Chem. Int. Ed., 41, 4563 (2002); doi:10.1002/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U.

J.W. Hartman, W.C. Hiscox and P.W. Jennings, J. Org. Chem., 58, 7613 (1993); doi:10.1021/jo00078a056.

W. Baidossi, M. Lahav and J. Blum, J. Org. Chem., 62, 669 (1997); doi:10.1021/jo961740m.

K. Imi, K. Imai and K. Utimoto, Tetrahedron Lett., 28, 3127 (1987); doi:10.1016/S0040-4039(00)96302-0.

H. Kanemitsu, K. Uehara, S. Fukuzumi and S. Ogo, J. Am. Chem. Soc., 130, 17141 (2008); doi:10.1021/ja807254d.

X. Jin, T. Oishi, K. Yamaguchi and N. Mizuno, Chem. Eur. J., 17, 1261 (2011); doi:10.1002/chem.201002761.

X.-F. Wu, D. Bezier and C. Darcel, Adv. Synth. Catal., 351, 367 (2009); doi:10.1002/adsc.200800666.

J.R. Cabrero-Antonino, A. Leyva-Pérez and A. Corma, Chem. Eur. J., 18, 11107 (2012); doi:10.1002/chem.201200580.

M.B.T. Thuong, A. Mann and A. Wagner, Chem. Commun., 48, 434 (2011); doi:10.1039/c1cc12928g.

B. Rao, W. Zhang, L. Hu and M. Luo, Green Chem., 14, 3436 (2012); doi:10.1039/c2gc36550b.

Z.-W. Chen, D.-N. Ye, Y.-P. Qian, M. Ye and L.-X. Liu, Tetrahedron, 69, 6116 (2013); doi:10.1016/j.tet.2013.05.057.

T. Tachinami, T. Nishimura, R. Ushimaru, R. Noyori and H. Naka, J. Am. Chem. Soc., 135, 50 (2013); doi:10.1021/ja310282t.

A.D. Allen, Y. Chiang, A.J. Kresge and T.T. Tidwell, J. Org. Chem., 47, 775 (1982); doi:10.1021/jo00344a006.

T. Suchimoto, T. Joya, E. Shirakawa and Y. Kawakami, Synlett, 1777 (2000); doi:10.1055/s-2000-8707.

N. Olive, E. Thomas, J.-F. Peyrat, M. Alami and J.-D. Brion, Synlett, 2175 (2004); doi:10.1055/s-2004-831310.

D.S. Noyce and K.E. DeBruin, J. Am. Chem. Soc., 90, 372 (1968); doi:10.1021/ja01004a030.

D.S. Noyce and M.D. Schiavelli, J. Am. Chem. Soc., 90, 1020 (1968); doi:10.1021/ja01006a030.

Z. Chen, J. Li, H. Jiang, S. Zhu, Y. Li and C. Qi, Org. Lett., 12, 3262 (2010); doi:10.1021/ol101251n.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

TFA-Mediated Alkyne Hydration Reaction to Synthesize Methyl Ketones

Corresponding Author(s) : Z.W. Chen

Abstract

Keywords

Full Article

Download Citation

References

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