纳米金催化(杂环)芳基酯与卤代烷经由C—O键活化的酯交换反应
收稿日期: 2018-09-21
修回日期: 2018-11-01
网络出版日期: 2018-11-26
基金资助
国家自然科学基金(Nos.21462031,21861030)、内蒙古自治区高等学校青年科技英才支持计划(No.NJYT-17-A22)、内蒙古师范大学基金(No.2013ZRYB10)资助项目.
Nano-Gold Catalyzed Transesterification of (Hetero) aryl Esters with Alkyl Halides via C-O Activation
Received date: 2018-09-21
Revised date: 2018-11-01
Online published: 2018-11-26
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462031, 21861030), the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (No. NJYT-17-A22) and the Project of Inner Mongolia Normal University (No. 2013ZRYB10).
麻鸿鹏 , 白朝鲁门 , 包永胜 . 纳米金催化(杂环)芳基酯与卤代烷经由C—O键活化的酯交换反应[J]. 有机化学, 2019 , 39(3) : 734 -746 . DOI: 10.6023/cjoc201809027
Nano-gold catalyzed transesterification of the (hetero) aryl ester with alkyl halides via C-O activation has been developed. In a series of supported AuNPs and PdNPs, the Au/γ-Al2O3 catalyst with an AuNP mean diameter of 3.63 nm and 3 wt% Au loading exhibited the best catalytic performance. The catalyst can be reused and shows high activity after five cycles. The X-ray photoelectron spectroscopy (XPS) analysis of the catalyst before and after the reaction suggested that the reaction might be performed via a catalytic cycle that began with Au0.
Key words: nano-gold catalyst; transesterification; halide
[1] (a) Otera, J.; Nishikido, J. Esterification:Methods, Reactions, and Application, Wiley, Hoboken, NJ, 2009, p. 1.
(b) Larock, R. C. Comprehensive Organic Transformation:A Guide to Functional Group Preparations, Wile-VCH, New York, 1999, Vol. 1, pp. 1~2640.
(c) Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M.; Stephenson, C. R. Nat. Chem. 2012, 4, 854.
(d) Takei, T. Advances in Catalysis, Elsevier, Tokyo, 2012, 55, pp. 1~126.
[2] (a) Haruta, M. Gold Bull. 2004, 37, 27.
(b) Hughes, M. D.; Xu, Y. J.; Jenkins, P.; McMorn, P.; Landon, P.; Enache, D. I.; Carley, A. F.; Attard, G. A.; Hutchings, G. J.; King, F.; Stitt, E. H.; Johnston, P.; Griffin, K.; Kiely, C. J. Nature 2005, 437, 1132.
(c) Haruta, M.; Ueda, A.; Tsubota, S.; Sanchez, R. M. T. Catal. Today 1996, 29, 443.
(d) Deng, X. Y.; Friend, C. M. J. Am. Chem. Soc. 2005, 127, 17178.
(e) Valden, M.; Lai, X.; Goodman, D. W. Science 1998, 281, 1647.
(f) Fu, Q.; Saltsburg, H.; Flytzani-Stephanopoulos, M. Science 2003, 301, 935.
(g) Hutchings, G. J. J. Catal. 1985, 96, 292.
(h) Hayashi, T.; Tanaka, K.; Haruta, M. J. Catal. 1998, 178, 566.
(i) Prati, L.; Rossi, M. J. Catal. 1998, 176, 552.
(j) Santra, A. K.; Kolmakov, A.; Yang, F.; Goodman, D. W. Science 1998, 281, 1647.
[3] (a) Mallat, T.; Baiker, A. Chem. Rev. 2004, 104, 3037.
(b) Prati, L.; Rossi, M. J. Catal. 1998, 176, 552.
[4] (a) Abad, A.; Concepción, P.; Corma, A.; García, H. Angew. Chem., Int. Ed. 2005, 44, 4066.
(b) Su, F. Z.; Liu, Y. M.; Wang, L. C.; Cao, Y.; He, H. Y.; Fan, K. N. Angew. Chem., Int. Ed. 2008, 47, 334.
(c) Abad, C. A.; Corma, A. A.; Garcia, H. Chem. Commun. 2006, 3178.
(d) Choudhary, V. R.; Dhar, A.; Jana, P.; Jha, R.; Uphade, B. S. Green Chem. 2005, 7, 768.
(e) Choudhary, V. R.; Dhar, A.; Jana, P. Green Chem. 2007, 9, 267.
(f) Wang, L. C.; Liu, Y. M.; Chen, M.; Cao, Y.; He, H. Y.; Fan, K. N. J. Phys. Chem. C 2008, 112, 6981.
(g) Wang, L.-C.; He, L.; Liu, Q.; Liu, Y.-M.; Chen, M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Appl. Catal., A:Chem. 2008, 344, 150.
(h) Su, F. Z.; Chen, M.; Wang, L. C.; Huang, X. S.; Liu, Y. M.; Cao, Y.; He, H. Y.; Fan, K. N. Catal. Commun. 2008, 9, 1027.
[5] (a) Biella, S.; Prati, L.; Rossi, M. J. Mol. Catal. A:Chem. 2003, 197, 207.
(b) Corma, A.; Domine, M. E. Chem. Commun. 2005, 4042.
(c) Marsden, C.; Taarning, E.; Hansen, D.; Johansen, L.; Klitgaard, S. K.; Egeblad, K.; Christensen, C. H. Green Chem. 2008, 10, 168.
(d) Fristrup, P.; Johansen, L. B.; Christensen, C. H. Chem. Commun. 2008, 2750.
(e) Laursen, A. B.; Hojholt, K. T.; Lundegaard, L. F.; Simonsen, S. B.; Helveg, S.; Schuth, F.; Paul, M.; Grunwaldt, J. D.; Kegnoes, S.; Christensen, C. H.; Egeblad, K. Angew. Chem., Int. Ed. 2010, 49, 3504.
(f) Xu, B.; Liu, X.; Haubrich, J.; Friend, C. M. Nat. Chem. 2011, 2, 61.
[6] (a) Grirrane, A.; Corma, A.; García, H. Science 2008, 322, 1661.
(b) Zhu, B.; Lazar, M.; Trewyn, B. G.; Angelici, R. J. J. Catal. 2008, 260, 1.
(c) Grirrane, A.; Corma, A.; García, H. J. Catal. 2009, 264, 138-144.
(d) Aschwanden, L.; Mallat, T.; Grunwaldt, J.-D.; Krumeich, F.; Baiker, A. J. Mol. Catal. A Chem. 2009, 300, 111.
(e) Ishida, T.; Kawakita, N.; Akita, T.; Haruta, M. Gold Bull. 2009, 42, 267-274.
(f) Zhu, B. Angelici, R. J. Chem. Commun. 2007, 2157.
[7] (a) Zhao, R.; Ji, D.; Lv, G.; Qian, G.; Yan, L.; Wang, X.; Suo, J. Chem. Commun. 2004, 904.
(b) Chen, L.; Hu, J.; Richards, R. J. Am. Chem. Soc. 2009, 131, 914.
(c) Wu, P.; Bai, P.; Loh, K. P.; Zhao, X. S. Catal. Today 2010, 158, 220.
(d) Wu, P.; Xiong, Z.; Loh, K. P.; Zhao, X. S. Catal. Sci. Technol. 2011, 1, 285.
(e) Lu, G.; Zhao, R.; Qian, G. Catal. Lett. 2004, 97, 115.
(f) Dapurkar, S. E.; Shervani, Z.; Yokoyama, T.; Ikushima, Y.; Kawanami, H. Catal. Lett. 2009, 130, 42.
[8] Fristrup, P.; Johansen, L. B.; Christensen, C. H. Chem. Commun. 2008, 2750.
[9] (a) Rodríguez, N.; Gooßen, J. L. Chem. Soc. Rev. 2011, 40, 5030.
(b) Correa, A.; Cornella, J.; Martin, R. Angew. Chem., Int. Ed. 2013, 52, 1878.
(c) Zarate, C.; Martin, R. J. Am. Chem. Soc. 2014, 136, 2236.
(d) Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422.
(e) Guan, B. T.; Wang, Y.; Li, B. J.; Yu, D. J.; Shi, Z. J. J. Am. Chem. Soc. 2008, 130, 14468.
(f) Yu, D. G.; Li, B. J.; Shi, Z. J. Acc. Chem. Res. 2010, 43, 1486.
(g) Takise, R.; Muto, K.; Yamaguchi, J.; Itami, K. Angew. Chem., Int. Ed. 2014, 53, 6791.
(h) Cornella, J.; Jackson, E. P.; Martin, R. Angew. Chem., Int. Ed. 2015, 54, 4075.
(i) Yang, J.; Chen, T.; Han, H. B. J. Am. Chem. Soc. 2015, 137, 1782.
(j) Gu, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 3187.
(k) Tobisu, M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem. Commun. 2011, 47, 2946.
(l) Guo, L.; Hsiao, C. C.; Yue, H.; Liu, X.; Rueping, M. ACS Catal. 2016, 6, 4438.
[10] (a) Muto, K.; Yamaguchi, J.; Musaev, D. G.; Itami, K. Nat. Commun. 2015, 6, 7508.
(b) Ben Halima, T.; Zhang, W.; Yalaoui, I.; Hong, X.; Yang, Y.-F.; Houk, K. N.; Newman, S. G. J. Am. Chem. Soc. 2017, 139, 1311.
(c) Pu, X.; Hu, J.; Zhao, Y.; Shi, Z. ACS Catal. 2016, 6, 6692.
(d) Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573.
(e) Guo, L.; Chatupheeraphat, A.; Rueping, M. Angew. Chem., Int. Ed. 2016, 55, 11810.
(f) Yamamoto, T.; Ishizu, J.; Kohara, T.; Komiya, S.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102, 3758.
[11] Bao, Y. S.; Baiyin, M.; Agula, B.; Jia, M. L.; Bao, Z. J. Org. Chem. 2014, 79, 6715.
[12] (a) Bianchi, C.; Porta, F.; Prati, L.; Rossi, M. Top. Catal. 2000, 13, 231.
(b) Porta, F.; Prati, L.; Rossi, M.; Coluccia, S.; Martra, G. Catal. Today 2000, 61, 165.
(c) Haruta, M.; Date, M. Appl. Catal., A 2001, 222, 427.
(d) Porta, F.; Prati, L.; Rossi, M.; Scari, G. J. Catal. 2002, 211, 464.
(e) Seker, E.; Gulari, E. Appl. Catal., A 2002, 232, 203.
(f) Xu, Q.; Kharas, K. C. C.; Datye, A. K. Catal. Lett. 2003, 85, 229.
(g) Grunwaldt, J. D.; Kiener, C.; Wogerbauer, C.; Baiker, A. J. Catal. 1999, 181, 223.
(h) Porta, F.; Rossi, M. J. Mol. Catal., A 2003, 204, 553.
(i) Biella, S.; Porta, F.; Prati, L.; Rossi, M. Catal. Lett. 2003, 90, 23.
[13] Chen, Y.; Somsen, C.; Milenkovic, S.; Hassel, A. W. J. Mater. Chem. 2009, 19, 924.
[14] Rozita, Y.; Brydson, R.; Comyn, T. P.; Scott, A, J.; Hammond, C.; Brown, A.; Chauruka, S.; Hassanpour, A.; Young, N. P.; Kirkland, A. I. ChemCatChem 2013, 5, 2695.
[15] Chen, J.; Namila, E.; Bai, C.; Baiyin, M.; Agula, B.; Bao, Y. S. RSC Adv. 2018, 8, 25168.
[16] Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597.
[17] Zhu, H. Y.; Ke, X. B.; Yang, X. Z.; Sarina, S.; Liu, H. W. Angew. Chem., Int. Ed. 2010, 49, 9657.
[18] Hu, Y.; Li, B. Tetrahedron 2017, 73, 7301.
[19] Kong, W.; Li, B.; Xu, X.; Song, Q. J. Org. Chem. 2016, 81, 8436.
[20] Farid, S. Y.; Robello, D. R.; Dinnocenzo, J. P.; Merkel, P. B.; Ferrar, L.; Roh, Y.; Mis, M. R. US 20050136357, 2005.
[21] Hosangadi, B.; Dave, R. H. Tetrahedron Lett. 1996, 37, 6375.
[22] Lee, P. H.; Lee, S. W.; Lee, K. Org. Lett. 2003, 5, 1103.
[23] Nakatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. Org. Lett. 2008, 10, 2067.
[24] Fel'dman, I. K.; Eidlin, A. M.; Sbornik, S. O. K. 1953, 1, 504.
[25] Wang, L.; Neumann, H.; Spannenberg, A.; Beller, M. Chem. Commun. 2017, 53, 7469.
[26] CAS NUMBER:1481434-06-3.
[27] Wang, G., Xu, Y., Zhang, S., Li, Z., Li, C. Green. Chem. 2017, 19, 4838.
[28] Koziakov, D., Jacobi von Wangelin, A. Org. Biom. Chem. 2017, 15, 6715.
[29] Ray, R.; Jana, R. D.; Bhadra, M.; Maiti, D.; Lahiri, G. K. Chem.-Eur. J. 2014, 20, 15618.
[30] Gao, M.; Chen, M.; Li, Y.; Tang, H.; Ding, H.; Wang, K.; Yang, L.; Li, C.; Lei, A. Asian J. Org. Chem. 2017, 6, 1566.
[31] CAS NUMBER:500344-32-1.
[32] Terakado, D.; Koutaka, H.; Oriyama, T. Tetrahedron:Asymmetry 2005, 16, 1157.
[33] Pathak, G.; Das, D.; Rokhum, L. RSC Adv. 2016, 6, 93729.
[34] Ren, L.; Wang, L.; Lv, Y.; Li, G.; Gao, S. Org. Lett. 2015, 17, 5172.
[35] Ayala, C. E.; Villalpando, A.; Nguyen, A. L.; McCandless, G. T.; Kartika, R. Org. Lett. 2012, 14, 3676.
[36] Chen, H.; Wang, G.; Han, J.; Xu, M.; Zhao, Y.; Xu, H. Tetrahedron 2014, 70, 212.
[37] Wang, Q.; Wang, Z.; Xu, Y.; Zhang, X.; Fan, X. Asian J. Org. Chem. 2016, 5, 1304.
[38] Zhang, X.; Xu, X.; Li, N.; Liang, Z.; Tang, Z. Tetrahedron 2018, 74, 1926.
/
| 〈 |
|
〉 |