Synthesis of a Carbene Complex and Its Application in Suzuki Reaction

doi:10.6023/cjoc201408028

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 705-711.DOI: 10.6023/cjoc201408028 Previous Articles Next Articles

ARTICLE

一种卡宾配合物的合成及其在Suzuki反应中的应用

唐演^a, 杨飞飞^a, 聂士鹏^a, 王林^a, 罗治斌^b, 陆鸿飞^a

a 江苏科技大学环境与化学工程学院镇江 212003;
b 江苏大学化工学院镇江 212003

收稿日期:2014-08-25 修回日期:2014-11-04 发布日期:2014-11-13
通讯作者: 陆鸿飞 E-mail:zjluhf1979@hotmail.com
基金资助:
国家自然科学基金(No. 21402067)资助项目.

Synthesis of a Carbene Complex and Its Application in Suzuki Reaction

Tang Yan^a, Yang Feifei^a, Nie Shipeng^a, Wang Lin Luo Zhibin^a, Lu Hongfei^b

a School of Envionmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003;
b School of Chemical Engineering, Jiangsu University, Zhenjiang 212003

Received:2014-08-25 Revised:2014-11-04 Published:2014-11-13
Supported by:
Project supported by the National Natual Science Foundation of China (No. 21402067).

1. Synthesis of a Carbene Complex and Its Application in Suzuki Reaction.PDF(1120KB)

Abstract

A palladium N-heterocyclic (NHC) complex has been synthesized and successfully developed as an efficient catalyst for the Suzuki coupling reaction of aryl bromides and 4-toluene sulfonic acid aromatic esters with aryl boronic acids. The catalytic reaction proceeded smoothly in dioxane with potassium acetate as the additive at 80 ℃ in an air atmosphere, while the yield of the target product is excellent and the catalyst can be synthesized easily.

Key words: Suzuki coupling reaction, carbene, palladium complex, synthesis

Cite this article

Tang Yan, Yang Feifei, Nie Shipeng, Wang Lin Luo Zhibin, Lu Hongfei. Synthesis of a Carbene Complex and Its Application in Suzuki Reaction[J]. Chin. J. Org. Chem., 2015, 35(3): 705-711.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Wei, S.-H.; Wang, C.; Wang, J.-W.; Cheng, K. Chin. J. Org. Chem. 2013, 33, 2402 (in Chinese). (韦珊红, 王晨, 王建伟, 程凯, 有机化学, 2013, 33, 2402.) (b) Chu, W.-Y.; Wang, M.; Li, X.-M.; Hou, Y.-J.; Sun, Z.-Z. Chin. J. Org. Chem. 2012, 32, 1666 (in Chinese). (初文毅, 王熳, 李新民, 侯艳君, 孙志忠, 有机化学, 2012, 32, 1666.) (c) Zhang, Y.; Yi, T.; Wang, K.; Fu, H.-Y.; Chen, H.; Li, R.-X. Chin. J. Org. Chem. 2012, 32, 790 (in Chinese). (张愚, 易韬, 王堃, 付海燕, 陈华, 李瑞祥, 有机化学, 2012, 32, 790.) (d) Liu, N.; Liu, C.; Jin, Z.-L. Chin. J. Org. Chem. 2012, 32, 860 (in Chinese). (刘宁, 刘春, 金子林, 有机化学, 2012, 32, 860.)
[2] Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
[3] Wu, X. F.; Anbarasan, Dr. P.; Neumann, Dr. H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047.
[4] (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. (b) Chung, K. H.; So, C. M.; Wong, S. M.; Luk, C. H.; Zhou, Z. Y.; Lau, C. P.; Kwong, F. Y. Chem. Commun. 2012, 48, 1967. (c) Tang, W. J.; Keshipeddy, S.; Zhang, Y. D.; Wei, X. D.; Savoie, J.; Patel, N. D.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2011, 13, 1366. (d) Leowanawat, P.; Zhang, N.; Safi, M.; Hoffman, D. J.; Fryberger, M. C.; George, A.; Percec, V. J. Org. Chem. 2012, 77, 2885. (e) Wang, Z. Y.; Chen, G. Q.; Shao, L. X. J. Org. Chem. 2012, 77, 6608. (f) Dubbaka, S. R.; Vogel, P. Org. Lett. 2004, 6, 95.
[5] Zim, D.; Lando, V. R.; Duponl, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
[6] Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
[7] Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049.
[8] Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher. C.; Artus, G. R. J. Angew. Chem., Int. Ed. 1995, 34, 2371.
[9] Skell, P. S.; Sandier, S. R. J. Am. Chem. Soc. 1958, 80, 2024.
[10] Wanzlick, H. W.; Schnherr, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
[11] (a) Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457. (b) Tang, Z. Y.; Spinella, S.; Hu, Q. S. Tetrahedron Lett. 2006, 47, 2427. (c) Gao, H.; Li, Y.; Zhou, Y. G.; Han, F. S.; Lin, Y. J. Adv. Synth. Catal. 2011, 353, 309. (d) Tang, Z. H.; Hu, Q. S. Adv. Synth. Catal. 2004, 346, 1635. (e) Xing, C. H.; Lee, J. R.; Tang, Z. Y.; Zheng, J. R.; Hu, Q. S. Adv. Synth. Catal. 2011, 353, 2051. (f) Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058.
[12] (a) Brenner, E.; Matt, D.; Henrion, M.; Teci, M.; Toupet, L. Dalton Trans. 2011, 40, 9889. (b) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A. M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346. (c) Chen, M. T.; Vicic, D. A.; Turner, M. T.; Navarro, O. Organometallics 2011, 30, 5052.
[13] Huang, J.; Hong, J. T.; Hong. S. H. Eur. J. Org. Chem. 2012, 2012, 6630.
[14] Wang, Z. Y.; Chen, G. Q.; Shao, L. X. J. Org. Chem. 2012, 77, 6608.
[15] (a) Berthon-Gelloz, G.; Siegler, M. A.; Spek, A. L.; Tinant, B.; Reek, J. N. H.; Markó, I. E. Dalton Trans. 2010, 39, 1444. (b) Yang, L. G.; Guan, P.; He, P.; Chen, Q.; Cao, C. S.; Peng, Y.; Shi, Z.; Pang, G. S.; Shi, Y. H. Dalton Trans. 2012, 41, 5010. (c) Meiries, S.; Speck, K.; Cordes, D. B.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2013, 32, 330. (d) Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. A. Chem. Eur. J. 2006, 12, 4749.
[16] Chartoire, A.; Frogneux, X.; Boreux, A.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 31, 6947.

一种卡宾配合物的合成及其在Suzuki反应中的应用

Synthesis of a Carbene Complex and Its Application in Suzuki Reaction

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du. N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 622-630.
[4]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[5]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[6]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[7]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[8]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[9]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[10]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[11]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[12]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[13]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[14]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[15]	Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.