Nano-Gold Catalyzed Transesterification of (Hetero) aryl Esters with Alkyl Halides via C-O Activation

doi:10.6023/cjoc201809027

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 734-746.DOI: 10.6023/cjoc201809027 Previous Articles Next Articles

Articles

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

麻鸿鹏, 白朝鲁门, 包永胜

内蒙古师范大学化学与环境科学学院内蒙古绿色催化重点实验室呼和浩特 010022

收稿日期:2018-09-21 修回日期:2018-11-01 发布日期:2018-11-26
通讯作者: 包永胜 E-mail:sbbys197812@163.com
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

Ma Hongpeng, Bai Chaolumen, Bao Yongsheng

College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot 010022

Received:2018-09-21 Revised:2018-11-01 Published:2018-11-26
Contact: 10.6023/cjoc201809027 E-mail:sbbys197812@163.com
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).

1. Nano-Gold Catalyzed Transesterification of (Hetero) aryl Esters with Alkyl Halides via C-O Activation.PDF(2607KB)

Abstract

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

Cite this article

Ma Hongpeng, Bai Chaolumen, Bao Yongsheng. Nano-Gold Catalyzed Transesterification of (Hetero) aryl Esters with Alkyl Halides via C-O Activation[J]. Chin. J. Org. Chem., 2019, 39(3): 734-746.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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.

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

Nano-Gold Catalyzed Transesterification of (Hetero) aryl Esters with Alkyl Halides via C-O Activation

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[2]	Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783.
[3]	Zhe Chang, Jiaxin Wang, Xi Lu, Yao Fu. Synthesis of gem-Difluoroalkenes through Nickel-Promoted Electrochemical Reductive Cross-Coupling [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 147-159.
[4]	Quancheng Li, Lan Jiang, Rui Bai, Yongkang Han, Zhengning Li. Progress in the Synthesis of 3-Substituted Phthaides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3390-3399.
[5]	Feng Han, Ting Wang, Bin Feng, Qing Xu. N,N-Dimethylformamide (DMF)-Promoted SpecificN-Alkylation of Hydroxyl N-Heterocycles with Organohalides: A Direct and Efficient Method for Synthesis of Pyridone Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2831-2838.
[6]	Buqing Cheng, Danhua Ge, Xin Wang, Xueqiang Chu. Perfluoroalkyl Halides as Fluorine-Containing Building Blocks for the Synthesis of Fluoroalkylated Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1925-1938.
[7]	Xu Xiuzhi, Zhang Fan, Huang Sheng, Zhang Zhiqiang, Ke Fang. Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2912-2918.
[8]	Qiu Huihua, Lin Baiyin, Zhou Peng, Zhang Jiantao, Liu Weibing. Researches on the Hydrodehalogenation of o-Triazole Aryl Halides in the System of Pd/C and Et₃N [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1372-1377.
[9]	Liu Wandong, Yang Yu, Li Jiaming, Guo Yanyan, Jin Fan, Zhang Bin. Design, Synthesis and Evaluation of Novel Tacrine-3-n-butylphthalide Hybrids as Multifunctional Cholinesterase Inhibitors [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3505-3515.
[10]	Yin, Qing, Yu, Xiaoqiang, Bao, Ming. A Novel Method for the Synthesis Triarylphosphines under Transition-Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2930-2935.
[11]	Ding Haixin, Li Chuang, Dong Xiangyou, Cao Banpen, Zhang Ning, Hong Sanguo, Xiao Qiang. First Total Synthesis of Marine Natural Nucleoside Kipukasin D [J]. Chin. J. Org. Chem., 2018, 38(12): 3351-3355.
[12]	Guo Fangjie, He Yuxuan, Wang Jingyun, Sun Jing, Zhou Mingdong. Potassium tert-Butoxide Promoted Formation of Alkyl Aryl Thioethers at Room Temperature: Synthesis and Mechanism [J]. Chin. J. Org. Chem., 2017, 37(6): 1556-1559.
[13]	Zhou Wen-Jun, Zhang Yihan, Cao Guangmei, Liu Huidong, Yu Da-Gang. Palladium-Catalyzed Radical-Type Transformations of Alkyl Halides [J]. Chin. J. Org. Chem., 2017, 37(6): 1322-1337.
[14]	Dong Xu, Hou Yongzheng, Meng Fanwei, Liu Hongbo, Liu Hui. Recent Advances on Alkyl-Heck Reaction [J]. Chin. J. Org. Chem., 2017, 37(5): 1088-1098.
[15]	Ma Xiaoli, Deng Ziyan, Yao Miaomiao, Zhong Mingdong, Li Wenling, Yang Zhi. Synthesis and Characterization of Two β-Diketiminato Tin(Ⅳ) Compounds [J]. Chin. J. Org. Chem., 2017, 37(5): 1300-1305.