Chinese Journal of Organic Chemistry >
Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes
Received date: 2017-01-27
Revised date: 2017-03-21
Online published: 2017-03-31
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21472092, 21172107), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
A copper iodide catalyzed reaction of aldehydes and t-butyl hydroperoxide (TBHP) was developed for the synthesis of peresters in the presence of bipyridine ligand under mild and neat conditions. The addition of bipyridine ligand increased the catalytic activities of copper catalyst significantly and triggered the reaction. The reaction showed good tolerance to various substrates, and good to excellent yields were obtained. Furthermore, a one-pot synthesis of allylic esters was also achieved by the addition of cyclohexene to the reaction mixture under neat condition at relative lower temperature.
Key words： copper catalyzed; N-donor ligand; C-H activation; perester; allylic ester; one-pot synthesis; neat
Xu Dingjian , Meng Lichen , Xu Hang , Yao Xiaoquan . Ligand-Triggered, Copper Catalyzed Synthesis of Peresters and Allylic Ester from Aldehydes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(5) : 1205 -1212 . DOI: 10.6023/cjoc201701051
[1] Some selected recent reviews: (a) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, DOI: 10.1021/acs.chemrev.6b00554.
(b) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(c) Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
(d) Hashiguchi, B. G.; Bischof, S. M.; Konnick, M. M.; Periana, R. A. Acc. Chem. Res. 2012, 45, 885.
(e) Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 2, 191.
(f) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(g) Lu, B.; Li, X.; Lin, Y. Chin. J. Org. Chem. 2015, 35, 2275 (in Chinese). (卢贝丽, 李现艳, 林咏梅, 有机化学, 2015, 35, 2275.)
(h) Tan, M.; Gu, Y.; Luo, X.; Zhang, P. Chin. J. Org. Chem. 2015, 35, 781 (in Chinese). (谭明雄, 顾运琼, 罗旭健, 张培, 有机化学, 2015, 35, 781.)
(i) Tang, H.; Huo, X.; Meng, Q. Acta Chim. Sinica 2016, 74, 219 (in Chinese). (汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
(j) Some recent examples
(j) Luo, F.; Long, Y.; Li, Z.; Zhou, X. Acta Chim. Sinica 2016, 74, 805 (in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
(k) Cheng, Q.; Xu, H.; Zhu, S.; Zhou, Q. Acta Chim. Sinica 2015, 73, 326 (in chinese) (程清卿, 许唤, 朱守非, 周其林, 化学学报, 2015, 73, 326.)
(l) Zhang, Z.; Li, J.; Huang, G.; Sun, K.; Zhang, G.; Ma, N.; Liu, Q.; Liu, T. Chin. J. Chem. 2016, 34, 1309.
(m) Wang, L.; Li, Z.; Qu, X.; Peng, W. Chin. J. Chem. 2015, 33, 1015.
[2] Some recent examples: (a) Sarkar, S.; Laha, R. M.; Mitra, R. N.; Maiti D. K. ACS Omega 2016, 1, 981.
(b) Tang, S.; Zeng, L.; Liu, Y.; Lei, A. Angew. Chem., Int. Ed. 2015, 54, 15850.
(c) Zhou, B.; Du, J.; Yang, Y.; Li, Y. Org. Lett. 2013, 15, 2934.
(d) Sharma, S.; Park, J.; Park, E.; Kim, A.; Kim, M.; Kwak, J. H.; Jung, Y. H.; Kim, I. S. Adv. Synth. Catal. 2013, 355, 332.
[3] Some examples: (a) Mo, J.; Wang, L.; Cui, X. Org. Lett. 2015, 17, 4960.
(b) Spantulescu, M. D.; Boudreau, M. A.; Vederas, J. C. Org. Lett. 2009, 11, 645.
(c) Yamago, S. J. Polym. Sci: Polym. Chem. Ed. 2006, 44, 1.
(d) Wang, L.; Liu, X.; Li, Y. Langmuir 1998, 14, 6879.
(e) Sosnovsky, G.; Zaret, E. H.; Konieczny, M. J. Org. Chem. 1972, 37, 2267 and the references therein.
[4] Lu, M. Y.; Bao, R.; Liu, W.; Li, Y. J. Org. Chem. 1995, 60, 5341.
[5] Bolje, A.; Hohloch, S.; Urankar, D.; Pevec, A.; Gazvoda, M.; Sarkar, B.; Košmrlj, J. Organometallics 2014, 10, 2588.
[6] Zhang, H.; Dong, D.-Q.; Hao, S.-H.; Wang, Z.-L. RSC Adv. 2016, 6, 8465.
[7] Wei, W.; Zhang, C.; Xu Y.; Wan, X. Chem. Commun. 2011, 47, 10827.
[8] (a) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819. For recent reviews see:
(b) Andrus, M. B.; Lashley, J. C. Tetrahedron 2002, 58, 845.
(c) Eames, J.; Watkinson, M. Angew. Chem., Int. Ed. 2001, 40, 3567.
[9] A recent review: Krylov, I. B.; Vil', V. A.; Terent'ev, A. O. Beilstein J. Org. Chem. 2015, 11, 92.
[10] Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384.
[11] Zhou, J.; Jin, C.; Li, X.; Su, W. RSC Adv. 2015, 5, 7232.
[12] Tran, B. L.; Driess, M.; Hartwig J. F. J. Am. Chem. Soc. 2014, 136, 17292.
[13] Zhao, J.; Fang, H.; Han, J.; Pan, Y. Org. Lett. 2014, 16, 2530.
[14] Rout, S. K.; Guin, S.; Ali, W.; Gogoi, A.; Patel, B. K. Org. Lett. 2014, 16, 3086.
[15] García-Cabeza, A. L.; Marín-Barrios, R.; Moreno-Dorado, F. J.; Ortega, M. J.; Massanet, G. M.; Guerra, F. M. Org. Lett., 2014, 16, 1598.
[16] Koschker, P.; Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011, 28, 20746.
[17] Thiery, E.; Aouf, C.; Belloy, J.; Harakat, D.; Bras, J. L.; Muzart, J. J. Org. Chem. 2010, 75, 1771.
[18] Recent reviews, see: Chem. Rev. 2008, 109(8), all of the articles therein; also see: Suzuki, M. Acc. Chem. Res. 2007, 40, 609.
[19] We also reported a series of reactions about the ligand effects on copper, silver and gold catalysts: (a) Yao, X.; Li, C.-J. Org. Lett. 2005, 7, 4395.
(b) Yao, X.; Li, C.-J. Org. Lett. 2006, 8, 1953.
(c) Yu, M.; Wang, Y.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2009, 50, 6791.
(d) Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett 2011, 2363.
(e) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Adv. Synth. Catal. 2012, 354, 71.
(f) Wang, Y.; Wu, C.; Nie, S.; Xu, D.; Yao, X. Tetrahedron Lett. 2015, 56, 6827.
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