A high-efficient method for the amidation of carboxylic acids promoted by triphenylphosphine oxide and oxalyl chloride
Lixue Jiang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorJing Yu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorFanfan Niu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorDerundong Zhang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorCorresponding Author
Xiaoling Sun
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Correspondence
Xiaoling Sun, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China.
Email: [email protected]
Search for more papers by this authorLixue Jiang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorJing Yu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorFanfan Niu
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorDerundong Zhang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Search for more papers by this authorCorresponding Author
Xiaoling Sun
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China
Correspondence
Xiaoling Sun, School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, China.
Email: [email protected]
Search for more papers by this authorAbstract
A effective amidation reaction of carboxylic acids with various amines promoted by triphenylphosphine oxide and oxalyl chloride under mild and neutral conditions has been developed. The feature of this procedure was the using and recycling of triphenylphosphine oxide at room temperature in 0.5 h. Furthermore a plausible mechanism also be deduced with the help of 31P NMR spectroscopy.
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References
- 1E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606.
- 2J. R. Dunetz, J. Magano, G. A. Weisenburger, Org. Process Res. Dev. 2016, 20, 140.
- 3C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827.
- 4V. R. Pattabiraman, J. W. Bode, Nature 2011, 480, 471.
- 5R. M. Lanigan, T. D. Sheppard, Eur. J. Org. Chem. 2013, 2013, 7453.
- 6J. Pitzer, K. J. Steiner, J. Biotechnol. 2016, 3, 17.
- 7M. M. Joullié, K. M. Lassen, Arkivoc 2010, 8, 189.
- 8H. Alinezhad, M. Tajbakhsh, M. Zare, M. Mousavi, Heteroatom Chem. 2016, 27, 290.
- 9J. B. Lee, J. Am. Chem. Soc. 1966, 88, 3440.
- 10H.-P. Buchstaller, H. M. Ebert, U. Anlauf, Synth. Commun. 2001, 31, 1001.
- 11A. Kumar, H. K. Akula, M. K. Lakshman, Eur. J. Org. Chem. 2010, 14, 2709.
- 12B. P. Bandgar, S. V. Bettigeri, Synth. Commun. 2004, 34, 2917.
- 13J. Garcia, F. Urpi, J. Vilarrasa, Tetrahedron Lett. 1984, 25, 4841.
- 14L. Barstow, V. Hrub, J. Org. Chem. 1971, 36, 1305.
- 15S. Yamada, Y. Takeuchi, Tetrahedron Lett. 1971, 12, 3595.
10.1016/S0040-4039(01)97239-9 Google Scholar
- 16C. Duangkamol, S. Jaita, S. Wangngae, Tetrahedron Lett. 2015, 56, 4997.
- 17J. R. Dunetz, Y. Q. Xiang, A. Baldwin, Org. Lett. 2011, 13, 5048.
- 18H. Chen, X. Xu, L. Liu, G. Tang, Y. Zhao, RSC Adv. 2013, 3, 16247.
- 19P.-J. Chen, H.-Y. Wang, A.-Y. Peng, RSC Adv. 2015, 5, 94328.
- 20Q. L. Luo, L. Lv, Y. Li, J. P. Tan, W. Nan, Q. Hui, Eur. J. Org. Chem. 2011, 43, 6916.
- 21D. C. Lenstra, F. P. J. T. Rutjes, J. Mecinovic, Chem. Commun. 2014, 50, 5763.
- 22C. J. O'Brien, J. L. Tellez, Z. S. Kang, A. L. Carter, S. R. Kunkel, K. C. Przeworski, G. A. Chass, Angew. Chem. Int. Ed. 2009, 48, 6836.
- 23C. J. O'Brien, F. Lavigne, E. E. Coyle, A. J. Holohan, B. J. Doonan, Chem. Eur. J. 2013, 19, 5854.
- 24C. J. O'Brien, Z. S. Nixon, A. J. Holohan, S. R. Kunkel, J. L. Tellez, B. J. Doonan, E. E. Coyle, F. Lavigne, L. J. Kang, K. C. Przeworski, Chem. Eur. J. 2013, 19, 15281.
- 25E. E. Coyle, B. J. Doonan, A. J. Holohan, K. A. Walsh, F. Lavigne, E. H. Krenske, C. J. O'Brien, Angew. Chem. Int. Ed. 2014, 53, 12907.
- 26H. A. van Kalkeren, J. Bruins, F. P. J. T. Rutjes, F. L. van Delft, Adv. Synth. Catal. 2012, 354, 1417.
- 27H. A. van Kalkeren, S. H. A. M. Leenders, C. R. A. Hommersom, F. P. J. T. Rutjes, F. L. van Delft, Chem. Eur. J. 2011, 17, 11290.
- 28H. A. van Kalkeren, F. L. van Delft, F. P. J. T. Rutjes, ChemSusChem 2013, 6, 1615.
- 29D. Hérault, D. H. Nguyen, D. Nuel, G. Buono, Chem. Soc. Rev. 2015, 44, 2508.
- 30M.-L. Schirmer, S. Jopp, J. Holz, A. Spannenberg, T. Werner, Adv. Synth. Catal. 2016, 358, 26.
- 31J. J. Cao, F. Zhou, J. Zhou, Angew. Chem. Int. Ed. 2010, 49, 4976.
- 32L. Chen, T. D. Shi, J. Zhou, Chem. Asian J. 2013, 8, 556.
- 33M. Masaki, K. Fukui, Chem. Lett. 1977, 6, 151.
- 34R. M. Denton, J. An, B. Adeniran, Chem. Commun. 2010, 46, 3025.
- 35R. M. Denton, J. An, B. Adeniran, A. J. Blake, W. Lewis, A. M. Poulton, J. Org. Chem. 2011, 76, 6749.
- 36R. M. Denton, X. P.-F. Tang, A. Przeslak, Org. Lett. 2010, 12, 4678.
- 37X. Tang, J. An, R. M. Denton, Tetrahedron Lett. 2014, 55, 799.
- 38R. M. Denton, J. An, P. Lindovska, W. Lewis, Tetrahedron 2012, 68, 2899.
- 39K. V. Rajendran, D. G. Gilheany, Chem. Commun. 2012, 48, 817.
- 40K. V. Rajendran, D. G. Gilheany, Chem. Commun. 2012, 48, 10040.
- 41K. V. Rajendran, J. S. Kudavalli, K. S. Dunne, D. G. Gilheany, Eur. J. Org. Chem. 2012, 14, 2720.
- 42P. A. Byrne, K. V. Rajendran, J. Muldoon, D. G. Gilheany, Org. Biomol. Chem. 2012, 10, 3531.
- 43K. Nikitin, M.-B. Helger, D. G. Gilheany, Chem. Commun. 2013, 49, 1434.
- 44N. P. Kenny, K. V. Rajendran, D. G. Gilheany, Chem. Commun. 2015, 51, 16561.
- 45R. Ramage, in Organophosphorus Reagents in Organic Synthesis (Ed: J. I. G. Cadogan), Academic Press, London 1979, pp. 511–535.
- 46R. Appel, M. Halstenberg, in Organophosphorus Reagents in Organic Synthesis (Ed: J. I. G. Cadogan), Academic Press, London 1979, pp. 387–432.
- 47T. Y. Yu, Y. Wang, P. F. Xu, Chem. Eur. J. 2014, 20, 98.
- 48M. Benaglia, S. Rossi, Org. Biomol. Chem. 2010, 8, 3824.
- 49S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 2008, 47, 1560.
- 50K. Fourmy, D. H. Nguyen, O. Dechy-Cabaretab, M. Gouygou, Catal. Sci. Technol. 2015, 5, 4289.
- 51S. Kotani, Y. Shimoda, M. Sugiura, M. Nakajima, Tetrahedron Lett. 2009, 50, 4602.
- 52M. Sugiura, N. Sato, S. Kotani, M. Nakajima, Chem. Commun. 2008, 36, 4309.
- 53D. Kurauchi, K. Hirano, H. Kato, T. Saito, K. Miyamoto, M. Uchiyama, Tetrahedron 2015, 71, 5849.
- 54S. Matsunaga, H. Qin, M. Sugita, S. Okada, T. Kinoshita, N. Yamagiwa, M. Shibasaki, Tetrahedron 2006, 62, 6630.
- 55S. Rommel, C. Belger, J.-M. Begouin, B. Plietker, ChemCatChem 2015, 7, 1292.
- 56L. Zhang, X.-J. Wang, J. Wang, N. Grinberg, D. Krishnamurthy, C. H. Senanayake, Tetrahedron Lett. 2009, 50, 2964.
- 57P. A. Byrne, K. V. Rajendran, J. Muldoon, D. G. Gilheany, Org. Biomol. Chem. 2012, 10, 3531.
- 58J. Einhorn, C. Einhorn, J.-L. Luche, Synth. Commun. 1990, 20, 1105.
- 59T. Taniguchi, D. Hirose, H. Ishibashi, ACS Catal. 2011, 1, 1469.
- 60S. M. Godfrey, C. A. McAuliffe, R. G. Pritchard, J. M. Sheffield, Chem. Commun. 1998, 8, 921.
- 61S. Wangngae, C. Duangkamol, M. Pattarawarapan, W. Phakhodee, RSC Adv. 2015, 5, 25789.
- 62R. A. Green, D. Pletcher, S. G. Leach, Org. Lett. 2016, 18, 1198.
- 63K. Bahrami, M. M. Khodaei, A. Farrokhi, Tetrahedron 2009, 65, 7658.
- 64S. E. Kim, H. Hahm, S. Kim, W. Jang, B. Jeon, Y. Kim, M. Kim, Asian J. Org. Chem. 2016, 5, 222.
- 65E. Valeur, M. Bradley, Tetrahedron 2007, 63, 8855.
- 66A. A. Lamar, L. S. Liebeskind, Tetrahedron Lett. 2015, 56, 6034.
- 67C. Duangkamol, S. Jaita, S. Wangngae, W. Phakhodee, M. Pattarawarapan, RSC Adv. 2015, 5, 52624.
- 68J. Liang, J. Lv, Z. Shang, Tetrahedron 2011, 67, 8532.
- 69C. M. Boehner, D. M. Marsden, H. F. Sore, D. Norton, D. R. Spring, Tetrahedron Lett. 2010, 51, 5930.
