Article
Solvent- and Metal-free Oxidative Esterification of Aromatic Aldehydes Using Urea-2,2-dihydroperoxypropane as a New Solid Oxidant
Kaveh Khosravi,
Kobra Khalaji,
Shirin Naserifar,
Corresponding Author
Kaveh Khosravi
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Corresponding author. Email: [email protected]; [email protected]Search for more papers by this authorKobra Khalaji
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Search for more papers by this authorShirin Naserifar
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Search for more papers by this authorKaveh Khosravi,
Kobra Khalaji,
Shirin Naserifar,
Corresponding Author
Kaveh Khosravi
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Corresponding author. Email: [email protected]; [email protected]Search for more papers by this authorKobra Khalaji
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Search for more papers by this authorShirin Naserifar
Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran
Search for more papers by this authorAbstract
Urea-2,2-dihydroperoxypropane as a noble and solid gem-dihydroperoxide derivative was used to transform various aromatic aldehydes to their corresponding benzoate derivatives in the presence of HBr under mild conditions at room temperature in high yields and short reaction times.
Supporting Information
| Filename | Description |
|---|---|
| jccs201600777-sup-0001-AppendixS1.docxWord 2007 document , 4.1 MB | Appendix S1. Physical and spectral data of UDHPP. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1 R. Gopinath, B. Barkakaty, B. Talukdar, B. K. Patel, J. Org. Chem. 2003, 68, 2944.
- 2(a) R. C. Larock, Comprehensive Organic Transformation, VCH, New York, NY, 1999; (b) D. R. Williams, F. D. Klingler, E. E. Allen, F. W. Lichtenthaler, Tetrahedron Lett. 1988, 29, 5087.
- 3 C. B. Kelly, M. A. Mercadante, R. J. Wiles, N. E. Leadbeater, Org. Lett. 2013, 15, 2222.
- 4(a) J. Otera, Esterification: Methods, Reaction and Application, 2nd ed., Wiley-VCH, Weinheim, 2010;
(b) W. Riemenschneider, H. M. Bolt, Esters, Organic. In Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005;
10.1002/14356007.a09_565.pub2 Google Scholar(c) D. V. Rosato, D. V. Rosato, M. V. Rosato, Plastic Product Material and Process Selection Handbook, Elesevier Inc., New York, NY, 2004.
- 5 C. F. Barnard, Organometallics 2008, 27, 5402.
- 6 J. N. Rosa, R. S. Reddy, N. R. Candeias, P. M. S. D. Cal, P. M. P. Gois, Org. Lett. 2010, 12, 2686.
- 7 C. Qin, H. Wu, J. Chen, M. Liu, J. Cheng, W. Su, J. Ding, Org. Lett. 2008, 10, 1537.
- 8 R. Gopinath, B. K. Patel, Org. Lett. 2000, 2, 577.
- 9 R. C. Larock, Comprehensive Organic Transformation, VCH, New York, NY, 1989, p. 840.
- 10 J. March, Advanced Organic Chemistry, New York, NY, John Wiley & Sons, 1992, p. 1196.
- 11 M. Tamura, T. Tonomura, K. I. Shimizu, A. Satsuma, Green Chem. 2012, 14, 984.
- 12 G. Jayachitra, N. Yasmeen, R. K. Srinivasa, S. L. Ralte, R. Srinivasan, A. K. Singh, Synth. Commun. 2003, 19, 3461.
- 13 A. Abiko, J. C. Roberts, T. Takemasa, S. Masamune, Tetrahedron Lett. 1986, 27, 4537.
- 14 B. O'Connor, G. Just, Tetrahedron Lett. 1987, 28, 3235.
- 15 G. Qian, R. Zhao, D. Ji, G. Lu, Y. Qi, J. Suo, Chem. Lett. 2004, 33, 834.
- 16 C. McDonald, H. Holcomb, K. Kennedy, E. Kirkpatrick, T. Leathers, P. Vanemon, J. Org. Chem. 1989, 54, 1213.
- 17 A. K. Sinha, A. Sharma, A. Swaroop, V. Kumar, Tetrahedron 2007, 63, 1000.
- 18 H. Sharghi, M. H. Sarvari, J. Org. Chem. 2003, 68, 4096.
- 19 J. H. Espenson, Z. Zhu, T. H. Zauche, J. Org. Chem. 1999, 64, 1191.
- 20 S. C. Thomason, D. G. Kubler, J. Chem. Educ. 1968, 45, 546.
- 21 R. Lerebours, C. Wolf, J. Am. Chem. Soc. 2006, 128, 13052.
- 22 J. Zhao, C. Mueck-Lichtenfeld, A. Studer, Adv. Synth. Catal. 2013, 355, 1098.
- 23 R. Grigg, T. R. B. Mitchell, S. Sutthivaiyakit, Tetrahedron 1981, 37, 4313.
- 24 W.-J. Yoo, C.-J. Li, Tetrahedron Lett. 2007, 48, 1033.
- 25
S. P. Chavan, S. W. Dantale, C. A. Govande, M. S. Venkatraman, C. Praveen, Synlett 2002, 2, 267.
10.1055/s-2002-19744 Google Scholar
- 26 S. Kiyooka, M. Ueno, E. Ishii, Tetrahedron Lett. 2005, 46, 4639.
- 27 X.-F. Wu, C. Darcel, Eur. J. Org. Chem. 2009, 8, 1144.
- 28 X.-F. Wu, Tetrahedron Lett. 2012, 53, 3397.
- 29 K. E. Kovi, C. Wolf, Chem. Eur. J. 2008, 14, 6302.
- 30 H. A. Staab, A. Mannschreck, Chem. Ber. 1962, 95, 1284.
- 31(a) O. Mitsunobu, Synthesis 1981, 1, 1; (b) R. Dembinski, Eur. J. Org. Chem. 2004, 13, 2763.
- 32 B. Neises, W. Steglich, Angew. Chem. Int. Ed. Engl. 1978, 17, 522.
- 33(a) Y. Dong, Mini-Rev. Med. Chem. 2002, 2, 113; (b) A. O. Terent'ev, A. V. Kutkin, Z. A. Starikova, M. Y. Antipin, Y. N. Ogibin, G. I. Nikishina, Synthesis 2004, 14, 2356; (c) R. Amewu, A. V. Stachulski, S. A. Ward, N. G. Berry, P. G. Bray, J. Davies, G. Labat, L. Vivas, P. M. O'Neill, Org. Biomol. Chem. 2006, 4, 4431.
- 34(a) P. Ghorai, P. H. Dussault, C. Hu, Org. Lett. 2008, 10, 2401; (b) Q. Zhang, Y. Li, Y.-K. Wu, Chin. J. Chem. 2007, 25, 1304.
- 35 A. O. Terent'ev, M. M. Platonov, A. I. Tursina, V. V. Chernyshev, G. I. Nikitina, J. Org. Chem. 2008, 73, 3169.
- 36(a) H.-S. Kim, Y. Nagai, K. Ono, K. Begum, Y. Wataya, Y. Hamada, K. Tsuchiya, A. Masuyama, M. Nojima, K. J. McCullough, J. Med.Chem. 2001, 44, 2357; (b) A. Masuyama, J.-M. Wu, M. Nojima, H.-S. Kim, Y. Wataya, Mini-Rev. Med. Chem. 2005, 5, 1035.
- 37(a) Y. Hamada, H. Tokuhara, A. Masuyama, M. Nojima, H. S. Kim, K. Ono, N. Ogura, Y. Wataya, J. Med. Chem. 2002, 45, 1374; (b) H. Hansma, A. Schroeder, AKZO N. V. Belg. Patent 868, 681, 1978; Chem. Abstr. 1979, 90, 153037a.
- 38 K. Jakka, J. Liu, C.-G. Zhao, Tetrahedron Lett. 2007, 48, 1395.
- 39 H. Saneyoshi, K. Miyata, K. Seio, M. Sekine, Tetrahedron Lett. 2006, 47, 8945.
- 40 A. O. Terent'ev, M. M. Platonov, A. V. Kutkin, Cent. Eur. J. Chem. 2006, 4, 207.
- 41(a) K. Khosravi, Res. Chem. Intermed. 2015, 41, 5253; (b) K. Khosravi, Cogent Chem. 2015, 1, 1002339; (c) K. Khosravi, M. Marashi, Org. Chem. Res. 2015, 1, 37; (d) K. Khosravi, Cogent Chem. 2015, 1, 1052615b; (e) K. Khosravi, S. Kazemi, J. Chin. Chem. Soc. 2012, 59, 641; (f) K. Khosravi, S. Kazemi, J. Chin. Chem. Soc. 2012, 59, 557; (g) K. Khosravi, S. Kazemi, Chin. Chem. Lett. 2012, 23, 387; (h) K. Khosravi, A. Asgari, J. Adv. Chem. 2015, 11, 3381.
- 42(a) M. Mirza-Aghayan, O. Zonoubi, M. M. Tavana, R. Boukherrou, Ultrason. Sonochem. 2015, 22, 359; (b) S. D. Guggilapu, S. K. Prajapti, B. N. Babu, Tetrahedron Lett. 2015, 56, 889; (c) J.-B. Feng, J.-L. Gong, Q. Li, X.-F. Wu, Tetrahedron Lett. 2014, 55, 1657; d) N. N. Karade, V. H. Budhewar, A. N. Katkar, G. B. Tiwari, ARKIVOC 2006, xi, 162; (e) K. R. Reddy, M. Venkateshwar, C. U. Maheswari, S. Prashanthi, Synth. Commun. 2009, 40, 186.
