Insight into Catalytic Properties of Supported Palladium Nanoparticles Catalyzed ortho-Directed Sulfonylation

doi:10.6023/cjoc202003020

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 1991-1998.DOI: 10.6023/cjoc202003020 Previous Articles Next Articles

负载纳米钯颗粒在邻位导向磺化反应中的催化特性探究

李鹏帅, 乌云, 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:2020-03-08 修回日期:2020-04-11 发布日期:2020-04-30
通讯作者: 包永胜 E-mail:sbbys197812@163.com
基金资助:
国家自然科学基金（No.21861030）和内蒙古自治区高等学校青年科技英才支持计划（No.NJYT-17-A22）资助项目.

Insight into Catalytic Properties of Supported Palladium Nanoparticles Catalyzed ortho-Directed Sulfonylation

Li Pengshuai, Wu Yun, Bai Chaolumen, Bao Yongsheng

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

Received:2020-03-08 Revised:2020-04-11 Published:2020-04-30
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21861030), and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (No. NJYT-17-A22).

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Abstract

Catalyzed by supported palladium nanoparticles, an ortho-directed sulfonylation reaction between 2-phenylpyri-dine and arylsulfonyl chlorides has been developed. The full oxidation-state change of palladium was detected in the X-ray photoelectron spectroscopy (XPS) analysis of the supported palladium nanoparticles catalyst before and after reaction, which confirmed that Pd-catalyzed ortho-directed sulfonylation reaction was performed via a Pd^Ⅱ/IV catalytic cycle instead of Pd^0/Ⅱ. The hot filtration test and other tests of catalysts further confirmed the hypothesis. This report afforded the most straightforward approach to confirm the variation of valence of palladium in ortho-directed sulfonylation reaction.

Key words: C-H functionalization, X-ray photoelectron spectroscopy (XPS) analysis, palladium nanoparticles catalyst, sulfonylation

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Li Pengshuai, Wu Yun, Bai Chaolumen, Bao Yongsheng. Insight into Catalytic Properties of Supported Palladium Nanoparticles Catalyzed ortho-Directed Sulfonylation[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1991-1998.

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[1] (a) Huang, Z.; Lim, H. N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764.
(b) Segawa, Y.; Maekawa, T.; Itami, K. Angew. Chem., Int. Ed. 2015, 54, 66.
(c) Ye, B.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308.
(d) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
[2] Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
[3] (a) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(b) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
(c) Ricci, P.; Krämer, K.; Cambeiro, X. C.; Larrosa, I. J. Am. Chem. Soc. 2013, 135, 13258.
(d) Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.
[4] (a) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
(b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
(c) Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234.
[5] Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302.
[6] (a) Liu, Y.-J.; Xu, H.; Kong, W.-J.; Shang, M.; Dai, H.-X.; Yu, J.-Q. Nature 2014, 515, 389.
(b) Yu, L.; Huang, Y. P.; Wei, Z.; Ding, Y. H.; Su, C. L.; Xu, Q. J. Org. Chem. 2015, 80, 8677.
[7] (a) Adak, L.; Bhadra, S.; Ranu, B. C. Tetrahedron Lett. 2010, 5, 3811.
(b) Williams, T. J.; Reay, A. J.; Whitwood, A. C.; Fairlamb, I. J. S. Chem. Commun. 2014, 50, 3052.
[8] (a) Basle, O.; Bidange, J.; Shuai, Q.; Li, C.-J. Adv. Synth. Catal. 2010, 352, 1145.
(b) Zhao, X.; Dimitrijevic, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466.
[9] (a) Trindade, A. F.; Gois, P. M. P.; Afonso, C. A. M. Chem. Rev. 2009, 109, 418.
(b) Climent, M. J.; Corma, A.; Iborra, S. Chem. Rev. 2011, 111, 1072.
(c) Li, C. L.; Sato, T.; Yamauchi, Y. Chem. Commun. 2014, 50, 11753.
[10] (a) Sun, J. W.; Fu, Y. S.; He, G. Y.; Sun, X. Q.; Wang, X. Catal. Sci. Technol. 2014, 4, 1742.
(b) Mandegani, Z.; Asadi, M.; Asadi, Z.; Mohajeri, A.; Iranpoor, N.; Omidvar, A. Green Chem. 2015, 17, 3326.
[11] (a) Coupry, D. E.; Butson, J.; Petkov, P. S.; Saunders, M.; Donnell, K. O.; Kim, H.; Buckley, C.; Addicoat, M.; Heine, T.; Szilágyi, P. Á. Chem. Commun. 2016, 52, 5175.
(b) Chen, L. Y.; Rangan, S.; Li, J.; Jianga, H. F.; Li, Y. W. Green Chem. 2014, 16, 3978.
(c) Fu, W. Q.; Feng, Y.; Fang, Z. X.; Chen, Q.; Tang, T.; Yua, Q. Y. Tang, T. D. Chem. Commun. 2016, 52, 3115.
[12] (a) Kishore, R. M.; Kantam, L.; Yadav, J.; Sudhakar, M.; Laha, S.; Venugopal, A. J. Mol. Catal. A: Chem. 2013, 379, 213.
(b) Jiao, Z. F.; Zhai, Z. Y.; Guo, X. N.; Guo, X. Y. J. Phys. Chem. C 2015, 119, 3238.
(c) Huang, J. P.; Wang, W.; Li, H. X. ACS Catal. 2013, 3, 1526.
[13] Zeng, M. F.; Du, Y. J.; Qi, C. Z.; Zuo, S. F.; Li, X. D.; Shao, L. J.; Zhang, X. M. Green Chem. 2011, 13, 350.
[14] Hu, J. Y.; Yang, Q. W.; Yang, L. F.; Zhang, Z. G.; Su, B. G.; Bao, Z. B.; Ren, Q. L.; Xing, H. B.; Dai, S. ACS Catal. 2015, 5, 6724.
[15] (a) Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014, 12, 9743.
(b) Xiao, F. H.; Chen, S. Q.; Tian, J. X.; Huang, H. W.; Liu, Y. J.; Deng, G. J. Green Chem. 2016, 18, 1538.
(c) Liang, S.; Zhang, R. Y.; Xi, L.Y.; Chen, S. Y.; Yu, X. Q. J. Org. Chem. 2013, 78, 11874.
(d) Reddy, L. R.; Hu, B.; Prashad, M.; Prasad, K. Angew. Chem., Int. Ed. 2009, 48, 172.
(e) Taniguchi, N. J. Org. Chem. 2015, 80, 1764.
[16] Xu, Y. F.; Liu, P.; Li, S. L.; Sun. P. P. J. Org. Chem. 2015, 80, 1269.
[17] Pillo, T.; Zimmermann, R.; Steiner, P.; Hüfner, S. J. Phys.: Condens. Matter 1997, 9, 3987.
[18] Zhang, D.; Zhaorigetu, B.; Bao, Y. S. J. Phys. Chem. C 2015, 119, 20426.
[19] (a) Joo, S. H.; Park, J. Y.; Tsung, C. K.; Yamada, Y.; Yang, P. D. Nat. Mater. 2009, 8, 126.
(b) Qiao, Z. A.; Zhang, P. F.; Chai, S. H.; Chi, M. F.; Veith, G. M.; Gallego, N. C.; Kidder, M.; Dai, S. J. Am. Chem. Soc. 2014, 136, 11260.
[20] Some report on the extensive Pd leaching of Pd/γ-Al₂O₃, see:(a) Brazier, J. B.; Nguyen, B. N.; Adrio, L. A.; Barreiro, E. M.; Leong, W. P.; Newton, M. A.; Figueroa, S. J. A.; Hellgardt, K.; Hii, K. K. M. Catal. Today 2014, 229, 95.
(b) Thathagar, M. B.; ten Elshof, J. E.; Rothenberg, G. Angew. Chem., Int. Ed. 2006, 45, 2886.
[21] Wang, F.; Yu, X.; Qi, Z.; Li, X. Chem.-Eur. J. 2016, 22, 511.
[22] Niu, L.; Yang, H.; Yang, D.; Fu, H. Adv. Synth. Catal. 2012, 354, 2211.

负载纳米钯颗粒在邻位导向磺化反应中的催化特性探究

Insight into Catalytic Properties of Supported Palladium Nanoparticles Catalyzed ortho-Directed Sulfonylation

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