Synthesis and Immobilization of Ether-Functionalized Phosphine for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (07): 1100-1106. Previous Articles Next Articles

Notes

醚功能化的膦配体的合成、负载及其在钯催化的Suzuki-Miyaura反应中的应用

于宏伟^1,2,3，官旻²，童庆松¹，贾莉¹，金子林²，施继成*^,1

(¹福建师范大学化学与材料学院福建省高分子材料重点实验室福州 350007)
(²大连理工大学精细化学国家重点实验室大连 116012)
(³石家庄学院化工学院石家庄 050035)

收稿日期:2010-07-25 修回日期:2011-01-31 发布日期:2011-02-23
通讯作者: 施继成 E-mail:jchshi@fjnu.edu.cn

Synthesis and Immobilization of Ether-Functionalized Phosphine for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Yu Hongwei^1,2,3 Guan Min² Tong Qing-song¹ Jia Li¹ Jin Zilin² Shi Jicheng*^,1

(¹Key Laboratory of Polymer Materials of Fujian Province, College of Chemistry and Mate-rials Science, Fujian Normal University, Fuzhou 350007)
(²State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012)
(³School of Chemical Engineering, Shijiazhuang University, Shijiazhuang 050035)

Received:2010-07-25 Revised:2011-01-31 Published:2011-02-23
Contact: Ji-cheng Shi E-mail:jchshi@fjnu.edu.cn

A new ether-functionalized ferrocenyl phosphine 3 has been prepared and immobilized on Mer-rifield resin. The phosphine 3 and the polymer-supported ferrocenyl phosphine 4 have been applied in palladium-catalyzed Suzuki-Miyaura reaction. These two catalytic systems can couple a range of aryl bromides with arylboronic acids to form the corresponding biaryls in excellent yields. The polymer-supported catalyst can be recycled without additional palladium.

Key words: phosphine, ether-functionalizing, immobilization, Pd catalyst, C—C bond-forming reaction

Cite this article

YU Hong-Wei, GUAN Min, TONG Qing-Song, JIA Li, JIN Zi-Lin, SHI Ji-Cheng. Synthesis and Immobilization of Ether-Functionalized Phosphine for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction[J]. Chin. J. Org. Chem., 2011, 31(07): 1100-1106.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1]1 B. Cornils, B.; Herrmann, W. A. (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, vol.2, Wiley-VCH/Verlag GmbH, Federal Republic of Germany, 2002, Chapter 3

[2]Shi, J. C.; Negishi, E. I. .[J].J. Organomet Chem,2003,687:518-

[3]Negishi, E. I.; Shi, J. C.; Zeng, X. .[J].Tetrahedron,2005,61:9886-

[4]Shi, J. C.; Zeng, X.; Negishi, E. I..[J].Org. Lett,2003,5:1825-

[5]5 Heck, R. F. Palladium Reagents in Organic Synthesis, Acdemic Press, New York, 1985

[6]6 Suzuki, A. Metal-Catalyzed Cross-Coupling Reactions, Diederich, F., Stang, P. J. (Eds.), Wiley-VCH, Weinheim, 1998, p. 49

[7]Yu, H.; Shi, J. C.; Zhang, H.; Yang, P.; Wang, X.; Jin, Z..[J].J. Mol. Catal. A: Chem,2006,250:15-

[8]Shi, J. C.; Cao, X.; Zheng, Y.; Jia, L.[J].有机化学,2007,27:666-

[9]9 Shi, J. C.; Yang, P.; Q. Tong, Y. Wu, Y. Peng,. [J].J. Mol. Catal. A: Chem.,2006,259:7-

[10]Shi, J. C.; Cao, X.; Zheng, Y.; Jia, L..[J].化学学报,2007,65:1702-

[11]Jia, L.; Yu, H.; Tong, Q.; Shi, J. C.; Jin, Z. .[J].有机化学,2008,28:1115-

[12]Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P..[J].J. Org. Chem,2004,69:3173-

[13]Herrmann, W. A.; Reisinger, C. P.; Spiegler, M. J..[J].Organomet. Chem,1998,557:93-

[14]Grasa, G. A.; Viciu, M. S.; Huang, J.;.[J].Organometallics,2003,21:2866-

[15]Littke, A. F.; Dai, C.; Fu, G. C..[J].J. Am. Chem. Soc,2000,122:4020-

[16]Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald, S. L..[J].J. Am. Chem. Soc,2002,124:1162-

[17]Old, D. W.; Wolfe, J. P.; Buchwald, S. L..[J].J. Am. Chem. Soc,1998,120:9722-

[18]Littke, A. F.; Fu, G. C..[J].Angew. Chem. Int. Ed,2002,41:4176-

[19]Walker, S. D.; Barder, T. E.; Martinnelli, J. K.;.[J].et al. Angew. Chem. Int. Ed,2004,43:1871-

[20]Parrish, C. A.; Buchwald, S. L..[J].J. Org. Chem,2001,66:3820-

[21]Phan, N. S.; Brown, D. H.; Styring, P. .[J].Tetrahedron Lett.,2004,45:7915-

[22]Kim, J.; Jun, B.; Byun, J.; Lee, Y. .[J].Tetrahedron Lett.,2004,45:5827-

[23]Guino, M.; Hii, K. K..[J].Tetrahedron Lett,2005,46:7363-

[24]Byun, J. Lee, Y. .[J].Tetrahedron Lett.,2004,45:1837-

[25]Xu, N.; Wang, Q.; Tao, F. .[J].有机化学,2005,25:458-

[26]Miura, M. Angew..[J].Chem. Int. Ed,2004,43:2201-

[27]Marcoux, J.; Wagaw, S.; Buchwald, S. L..[J].J. Org. Chem,1997,62:1568-

[28]Yu, H.; Tong, Q.; Peng, P.; Jia, L.; Shi, J. C.; Jin, Z. .[J].Chin. Chem. Lett,2007,18:37-

[29]Gischig, S.; Togni, A..[J].Organometallics,2004,22:2479-

[30]Hu, Q.; Lu, Y.; Tang, Z.; Yu, H. J..[J].Am. Chem. Soc,2003,125:2856-

[31]Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P..[J].Organometallics,2002,21:2866-

醚功能化的膦配体的合成、负载及其在钯催化的Suzuki-Miyaura反应中的应用

Synthesis and Immobilization of Ether-Functionalized Phosphine for Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[2]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[3]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[4]	Juan Tang, Jiayu Hu, Zhiqiang Zhu, Shouzhi Pu. Recent Advances in Visible-Light-Induced Organic Phosphine- Promoted Deoxygenative Functionalization Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4036-4056.
[5]	Yushan Zhang, Zhen Huan, Jindong Yang, Jinpei Cheng. Recent Advances in Hydrogen Transfer Reactivities of N-Heterocyclic Phosphines [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3806-3825.
[6]	Zhiyuan Chen, Mengwei Yang, Jianlin Xu, Yunhe Xu. Regioselective Synthesis of β-Silyl-Substituted Vinylphosphine Oxides via Copper-Catalyzed Protosilylation of Dialkynylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3598-3607.
[7]	Jingjie Li, Yuhao Wang, Tiantian Meng, Yiyong Huang. Phosphine-Catalyzed Synthesis of 1,3-Dihydro-3-alkylidene-2H-indol-2-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2222-2228.
[8]	Zheng Li, Yingchun Gu, Dazhen Xu, Xuening Fei, Lei Zhang. Density Functional Theory Study on the Mechanism of Organophosphine-Catalyzed [4+2] Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 830-837.
[9]	Hongxia Ren, Mengmeng Ma, You Huang. Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3129-3142.
[10]	Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.
[11]	Huan Liu, Xufeng Lin, Da Yang. Novel Ir-Complexes for Hydroformylation of Olefins with H₂O as the Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3571-3577.
[12]	Xinchan Lan, Lili Wang, Zheng Duan, François Mathey. Synthesis of 2-Pyrenylphosphines via Phospho-Fries Rearrangement [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1153-1160.
[13]	Jinwei Yuan, Yan Liu, Yuanyuan Ge, Shaoxuan Dong, Saiyi Song, Liangru Yang, Yongmei Xiao, Shouren Zhang, Lingbo Qu. Visible-Light-Induced Regioselective ortho-C—H Phosphonylation of β-Naphthols with Diarylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4738-4748.
[14]	Yuanting Huang, Qian Chen. Recent Advances in C(sp³)—H Phosphorylation Based on Secondary Phosphine Oxides and Phosphite Esters [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4138-4153.
[15]	Wei Cai, You Huang. Advances in Organophosphorus Redox Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3903-3913.