Synthesis of (Ph3P)2PdX2 Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate

doi:10.1007/s40242-017-7125-7

高等学校化学研究 ›› 2017, Vol. 33 ›› Issue (6): 860-863.doi: 10.1007/s40242-017-7125-7

Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate

LIU Chengxin, HAN Fangwai, LIU Guiyan, ZHAO Hongkun

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-organic Hybrid Functional Material Chemistry(Tianjin Normal University), Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China

收稿日期:2017-03-31 修回日期:2017-05-21 出版日期:2017-12-01 发布日期:2017-06-05
通讯作者: LIU Guiyan,E-mail:guiyanliu2013@163.com;ZHAO Hongkun,E-mail:hxxyzhk@mail.tjnu.edu.cn E-mail:guiyanliu2013@163.com;hxxyzhk@mail.tjnu.edu.cn
基金资助:
Supported by the Natural Science Foundation of Tianjin, China(No.16JCYBJC19700) and the Innovation Team Plan of the Tianjin Education Committee, China(No.TD12-5037).

Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate

LIU Chengxin, HAN Fangwai, LIU Guiyan, ZHAO Hongkun

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-organic Hybrid Functional Material Chemistry(Tianjin Normal University), Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China

Received:2017-03-31 Revised:2017-05-21 Online:2017-12-01 Published:2017-06-05
Contact: LIU Guiyan,E-mail:guiyanliu2013@163.com;ZHAO Hongkun,E-mail:hxxyzhk@mail.tjnu.edu.cn E-mail:guiyanliu2013@163.com;hxxyzhk@mail.tjnu.edu.cn
Supported by:
Supported by the Natural Science Foundation of Tianjin, China(No.16JCYBJC19700) and the Innovation Team Plan of the Tianjin Education Committee, China(No.TD12-5037).

摘要/Abstract

摘要： Two palladium complexes, (Ph₃P)₂PdBr₂ and (Ph₃P)₂PdI₂, were synthesized by a new method and their structures were confirmed by NMR, elemental analysis and X-ray crystallography. The catalytic activity of the two palladium complexes was evaluated in Mizoroki-Heck cross-coupling reaction of aryl halide with acrylate, and the results show that they all have high catalytic activity to many different substrates.

关键词: Palladium catalyst, Triphenylphosphine ligand, Mizoroki-Heck reaction

Abstract: Two palladium complexes, (Ph₃P)₂PdBr₂ and (Ph₃P)₂PdI₂, were synthesized by a new method and their structures were confirmed by NMR, elemental analysis and X-ray crystallography. The catalytic activity of the two palladium complexes was evaluated in Mizoroki-Heck cross-coupling reaction of aryl halide with acrylate, and the results show that they all have high catalytic activity to many different substrates.

Key words: Palladium catalyst, Triphenylphosphine ligand, Mizoroki-Heck reaction

LIU Chengxin, HAN Fangwai, LIU Guiyan, ZHAO Hongkun. Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate[J]. 高等学校化学研究, 2017, 33(6): 860-863.

参考文献

[1] Oestrich M., The Mizoroki_Heck Reaction, John Wiley & Sons:West Sussex, U. K., 2009
[2] Albéniz A. C., Carrera N., Eur. J. Inorg. Chem., 2011, 15, 2347
[3] Yin J., Ding S. M., Zeng L., Xia H., Chen C., Zhang N., Chem. J. Chinese Universities, 2015, 36(4), 720
[4] Liu Y., Li M., Lu Y., Wu H. H., Gao G. H., Chem. J. Chinese Universities, 2007, 28(4), 723
[5] Wang Y. C., Li X. Y., Li Y. J., Pan Y. M., Cheng K. G., Wang H. S., Chem. Res. Chinese Universities, 2014, 30(4), 614
[6] Molnár Á., Chem. Rev., 2011, 111, 2251
[7] David W. O., John P. W., Stephen L. B., J. Am. Chem. Soc., 1998, 120, 9722
[8] Yang B. H., Buchwald S. L., J. Am. Chem. Soc., 1999, 121, 9550
[9] Bei X., Turner H. W., Weinberg W. H., Guram A. S., Petersen J. L., J. Org. Chem., 1999, 64, 6797
[10] Littke A. F., Fu G. C., Angew. Chem. Int. Ed., 1998, 37, 3387
[11] Littke A. F., Fu G. C., J. Am. Chem. Soc., 2001, 123, 6989
[12] Andreu M. G., Zapf A., Beller M., Chem. Commun., 2000, (24), 2475
[13] Bedford R. B., Cazin C. S. J., Chem. Commun., 2001, 1540
[14] Schnyder A., Indolese A. F., Studer M., Blaser H. U., Angew. Chem. Int. Ed., 2002, 41, 3668
[15] Jesse R. M., Glenn P. A. Y., Donald A. W., J. Am. Chem. Soc., 2014, 136, 10166
[16] Brad P. C., John F. H., J. Am. Chem. Soc., 2010, 132, 79
[17] Matthew G. L., Mallory K. T., Kevin H. S., J. Org. Chem., 2014, 79, 10837
[18] Zapf A., Beller M., Chem. Eur. J., 2000, 6, 1830
[19] Montserrat D., Oscar P., Accounts Chem. Res., 2010, 43, 312
[20] Piet W. N. M. L., Paul C. J. K., Carmen C., Oscar P., Montserrat D., Chem. Rev., 2011, 111, 2077
[21] Yvette M., Montserrat D., Oscar P., Carmen C., Org. Lett., 2005, 7, 25
[22] Li G. Y., Angew. Chem. Int. Ed., 2001, 40, 1513
[23] Arun K., Gyandshwar K. R., Satyendra K., Ajai K. S., Organometallics, 2014, 33, 2921
[24] Chang Y. C., Chang W. C., Hu C. Y., Hong F. E., Organometallics, 2014, 33, 3523
[25] Lucas R. M., Elizabeth C. W., Raluca C., Jason M. S., David A. D., Kevin P. O., Kevin H. S., Organometallics, 2008, 27, 577
[26] Shirin N., Mohammad J., Ezzat R., Organometallics, 2009, 28, 6281
[27] Park S. B., Alper H., Org. Lett., 2003, 5, 3209
[28] Wang C., Fu Y., Li Z., Guo Q. X., Chin. J. Chem., 2008, 26, 358
[29] Herrmann W. A., Brossmer C., Reisinger C. P., Riermeier T. H., Ofele R. K., Beller M., Chem. Eur. J., 1997, 3, 1357
[30] Gareth W. V. C., Wiliam E., Jonathan P. R., Acta Cryst., 1999, C55, 320
[31] Andrein B. P., Gazzetta Chimica Italiana, 1988, 118, 469
[32] Autschbach J., Sutter K., Truflandier A. L., Brendler E., Wagler J., Chem. Eur. J., 2012, 18, 12803
[33] Crawforth M. C., Burling S., Fairlamb J. S. I., Kapdi A. R., Taylor J. K. R., Whitwood C. A., Tetrahedron, 2005, 61, 9736
[34] Lo K. M., Ng S. W., Acta Cryst., 2009, E65, m940
[35] Theissmanna T., Bolteb M., Acta Cryst., 2006, E62, m1056
[36] Dolomanov O. V., Bourhis L. J., Gildea R. J., Howard J. A. K., Puschmann H. J., Appl. Cryst., 2009, 42, 339
[37] Sheldrick G. M., Acta Cryst., 2015, A71, 3

Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate

Synthesis of (Ph₃P)₂PdX₂ Complexes and Their Catalytic Activity for Heck Reaction Involving Aryl Halide and Acrylate

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价

[1]	XI Xiang-li, ZHU Jing, CAO Shao-kui. Catalytic Hydrogenation over Palladium Complex of Molecular Complex of Poly(4-vinylpyridine) with Acetic Acid[J]. 高等学校化学研究, 2003, 19(1): 76-79.
[2]	WU Shi-hua, WEI Wei, ZHU Chang-ying, HUANG wei-ping, ZHANG Shou-min, ZHENG Xiu-cheng, ZHANG Shu-hong, ZHAO Wei-jun. Effects of the Specific Area and the Thermal Stability of a Polymer on the Catalytic Activities of Polymer Immobilized Co-Pd Catalysts by SAMI[J]. 高等学校化学研究, 2001, 17(4): 439-444.
[3]	DU Jin-xing, HUANG Xian. Synthesis of (2E)-α,β-Unsaturated AmidesCatalyzed by Micro Palladium Under Solid-LiquidPhase-Transfer Conditions[J]. 高等学校化学研究, 1995, 11(1): 71-74.