Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a <i>N</i>-phenyl framework

引用本文: Dong-Dong Zhang, Yun-Long Liu, Yan Wang, Hao Wei, Min Shi, Fei-Jun Wang. Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework[J]. Chinese Chemical Letters, 2016, 27(4): 563-565. shu

Citation: Dong-Dong Zhang, Yun-Long Liu, Yan Wang, Hao Wei, Min Shi, Fei-Jun Wang. Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework[J]. Chinese Chemical Letters, 2016, 27(4): 563-565. shu

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China;
b School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China;
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
基金项目:
The authors acknowledge the National Natural Science Foundation of China for financial support (Nos. 21372075 and 61376003).

摘要: A family of tropos ligands bearing a N-heterocyclic carbene and a chiral oxazoline coordination group with a N-phenyl framework were easily prepared, and their coordination behavior with Pd(II) acetate was performed, affording a series of axially chiral palladium complexes in good yields.

关键词:

tropos ligand
/ Copper catalyzed cross-coupling of N-C
/ bond
/ Axially chiral
/ Palladium complex
/ N-Phenyl framework

English

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China;
b School of Electronic Information and Electrical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China;
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Received Date: 10 December 2015
Revised Date: 07 January 2016
Available Online: 01 February 2016
Fund Project:
The authors acknowledge the National Natural Science Foundation of China for financial support (Nos. 21372075 and 61376003).

Abstract: A family of tropos ligands bearing a N-heterocyclic carbene and a chiral oxazoline coordination group with a N-phenyl framework were easily prepared, and their coordination behavior with Pd(II) acetate was performed, affording a series of axially chiral palladium complexes in good yields.

Key words:

tropos ligand
/ Copper catalyzed cross-coupling of N-C
/ bond
/ Axially chiral
/ Palladium complex
/ N-Phenyl framework

1. [1] J.D. Morrison, Asymmetric Synthesis, Academic Press, New York, 1985, p. 5.
2. [2] R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994.
3. [3] E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, I-III, Springer, Berlin, 1999.
4. [4] I. Ojima, Catalytic Asymmetric Synthesis, 2nd ed., Wiley-VCH, New York, 2000.
5. [5] A. Miyashita, A. Yasuda, H. Takaya, et al., Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of α-(acylamino) acrylic acids, J. Am. Chem. Soc. 102(1980) 7932-7934.
6. [6] R. Noyori, Asymmetric catalysis:science and opportunities, Angew. Chem. Int. Ed. 41(2002) 2008-2022.
7. [7] F. Wang, Y.J. Zhang, H. Wei, J. Zhang, W. Zhang, Atropisomeric bisoxazoline ligands with a bridge across the 5,5'-position of biphenyl for asymmetric catalysis, Tetrahedron Lett. 48(2007) 4083-4086.
8. [8] H. Wei, Y.J. Zhang, F. Wang, W. Zhang, Novel atropisomeric bisphosphine ligands with a bridge across the 5,5'-position of biphenyl for asymmetric catalysis, Tetrahedron:Asymmetry 19(2008) 482-488.
9. [9] Y.J. Zhang, F. Wang, W. Zhang, Chelation-induced axially chiral palladium complex system with tetraoxazoline ligands for highly enantioselective Wacker-type cyclization, J. Org. Chem. 72(2007) 9208-9213.
10. [10] H. Yu, F. Xie, Z. Ma, Y. Liu, W. Zhang, Switchable stereoselectivity:the effects of substituents on the D₂-symmetric biphenyl backbone of phosphoramidites in copper-catalyzed asymmetric conjugate addition reactions with triethylaluminium, Adv. Synth. Catal. 354(2012) 1941-1947.
11. [11] J. Chen, D. Liu, N. Butt, et al., Palladium-catalyzed asymmetric hydrogenation of aacyloxy-1-aryletheanones, Angew. Chem. Int. Ed. 52(2013) 11632-11636.
12. [12] F. Wang, S. Li, M. Qu, et al., A highly efficient kinetic resolution of Morita-Baylis-Hillman adducts achieved by N-Ar axially chiral Pd-complexes catalyzed asymmetric allylation, Chem. Commun. 47(2011) 12813-12815.
13. [13] F. Wang, S. Li, M. Qu, et al., Synthesis of axially chiral oxazoline-carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂, Beilstein J. Org. Chem. 8(2012) 726-731.
14. [14] Q. Xu, P. Gu, F. Wang, M. Shi, Selectfluor promoted NHC-oxazoline gold(I) complex catalyzed cycloaddition/oxidation reaction of enynones with alkenes, Org. Chem. Front. 2(2015) 1475-1484.
15. [15] Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, Novel axial chiral catalyst derived from biphenyl ligands bearing only two ortho-substituents, Tetrahedron Lett. 38(1997) 2681-2684.
16. [16] H.A. McManus, P.J. Guiry, Recent developments in the application of oxazolinecontaining ligands in asymmetric catalysis, Chem. Rev. 104(2004) 4151.
17. [17] F. Tian, D. Yao, Y. Liu, F. Xie, W. Zhang, Iridium-catalyzed highly enantioselective hydrogenation of exocyclic α,β-unsaturated carbonyl compounds, Adv. Synth. Catal. 352(2010) 1841-1845.
18. [18] Y. Imai, W. Zhang, T. Kida, Y. Nakatsuji, I. Ikeda, Novel chiral bisoxazoline ligands with a biphenyl backbone:preparation, complexation, and application in asymmetric catalytic reactions, J. Org. Chem. 65(2000) 3326-3333.
19. [19] W. Zhang, F. Xie, S. Matsuo, et al., Bisoxazoline ligands with an axial-unfixed biaryl backbone:the effects of the biaryl backbone and the substituent at oxazoline ring on Cu-catalyzed asymmetric cyclopropanation, Tetrahedron:Asymmetry 17(2006) 767-777.
20. [20] F. Wang, Y.J. Zhang, G. Yang, W. Zhang, Pd(II)-catalyzed Wacker-type cyclization of 2-allylphenols by use of bisoxazoline ligands with axial-unfixed biphenyl, Tetrahedron Lett. 48(2007) 4179-4182.
21. [21] F. Wang, L.J. Liu, W. Wang, S. Li, M. Shi, Chiral NHC-metal-based asymmetric catalysis, Coord. Chem. Rev. 256(2012) 804-853.

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沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

English

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

English

Synthesis of axially chiral oxazoline-carbene coordinated palladium complexes with a N-phenyl framework

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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