Modular Approach to the Synthesis of Polydentate NHC-Ligand Precursors (Benzimidazolium Salts) Containing Axial Chiral 1,1′-Binaphthyl via Pd-Catalyzed N-Arylation of 1,2-Diaminobenzene

Shifa Zhu; Chao Wang; Songxian Zhao; Yelin Xiao; Lang Hu; Zhipeng Huang

doi:10.1055/s-0033-1340286

Synthesis, Table of Contents

Synthesis 2014; 46(02): 212-224
DOI: 10.1055/s-0033-1340286

paper

Modular Approach to the Synthesis of Polydentate NHC-Ligand Precursors (Benzimidazolium Salts) Containing Axial Chiral 1,1′-Binaphthyl via Pd-Catalyzed N-Arylation of 1,2-Diaminobenzene

Shifa Zhu*

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

,

Chao Wang

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

,

Songxian Zhao

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

,

Yelin Xiao

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

,

Lang Hu

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

,

Zhipeng Huang

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China Fax: +86(20)87113735 Email: zhusf@scut.edu.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

A convenient and efficient modular approach to the synthesis of polydentate NHC ligand precursors (benzimidazolium salts) containing axial chiral 1,1′-binaphthyl from 1,2-diaminobenzene and BINOL has been developed. The benzimidazolium salts could be regarded as the potential bidentate, tridentate, and tetradentate NHC ligand precursors.

Key words

NHC - benzimidazolium salt - N-arylation - Pd-catalyzed

Full Text

References

References

1a Fröhlich N, Pidun U, Stahl M, Frenking G. Organometallics 1997; 16: 442
1b Boehme C, Frenking G. Organometallics 1998; 17: 5801
1c Bourissou D, Guerret O, Gabbai FP, Bertrand G. Chem. Rev. 2000; 100: 39
1d Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1290
1e Cesar V, Bellemin-Laponaz S, Gade LH. Chem. Soc. Rev. 2004; 33: 619
1f Hahn FE. Angew. Chem. Int. Ed. 2006; 45: 1348
1g O’Brien CJ, Organ MG. Angew. Chem. Int. Ed. 2007; 46: 2768
1h Hahn FE, Jahnke MC. Angew. Chem. Int. Ed. 2008; 47: 3122
1i Zeitler K. Angew. Chem. Int. Ed. 2005; 44: 7506
1j Christmann M. Angew. Chem. Int. Ed. 2005; 44: 2632
1k Enders D, Balensiefer T. Acc. Chem. Res. 2004; 37: 534
1l Winkel A, Reddy PV. G, Wilhelm R. Synthesis 2008; 999
1m Baudequin C, Bregeon D, Levillain J, Guillen F, Plaquevent JC, Gaumont AC. Tetrahedron: Asymmetry 2005; 16: 3921
1n Baudequin C, Baudoux J, Levillain J, Cahard D, Gaumont AC, Plaquevent JC. Tetrahedron: Asymmetry 2003; 14: 3081
1o Ding J, Armstrong DW. Chirality 2005; 17: 281
1p Bica K, Gaertner P. Eur. J. Org. Chem. 2008; 3235
1q Zhu S, Liang R, Jiang H. Tetrahedron 2012; 68: 7949
1r Zhu S, Liang R, Chen L, Wang C, Ren Y, Jiang H. Tetrahedron Lett. 2012; 53: 815

2a N-Heterocyclic Carbenes in Synthesis . Nolan SP. Wiley-VCH; Weinheim: 2006
2b Glorius F. N-Heterocyclic Carbenes in Transition Metal Catalysis. Springer; Berlin: 2007

3 Waltman AW, Grubbs RH. Organometallics 2004; 23: 3105

4a Atwood DA, Harvey MJ. Chem. Rev. 2001; 101: 37
4b Katsuki T. Synlett 2003; 281
4c Cozzi PG. Chem. Soc. Rev. 2004; 33: 410
4d Katsuki T. Chem. Soc. Rev. 2004; 33: 437
4e Darensbourg DJ, Mackiewicz RM, Phelps AL, Billodeaux DR. Acc. Chem. Res. 2004; 37: 836
4f Venkataramanan NS, Kuppuraj G, Rajagopal S. Coord. Chem. Rev. 2005; 249: 1249
4g Baleizao C, Garcia H. Chem. Rev. 2006; 106: 3987

5 Zhu S, Wang C, Chen L, Liang R, Yu Y, Jiang H. Org. Lett. 2011; 13: 1146

6a Wang HM. J, Lin IJ. B. Organometallics 1998; 17: 972
6b Lin JC. Y, Huang RT. W, Lee CS, Bhattacharyya A, Hwang WS, Lin IJ. B. Chem. Rev. 2009; 109: 3561
6c Díez-Gonzalez S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612

7a Muniz K. Adv. Synth. Catal. 2004; 346: 1425
7b Muehlhofer M, Strassner T, Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1745

8a Marion N, Nolan SP. Acc. Chem. Soc. 2008; 41: 1440
8b Romao CC, Kühn FE, Herrmann WA. Chem. Rev. 1997; 97: 3197
8c Stahl SS, Thorman JL, Nelson RC, Kozee MA. J. Am. Chem. Soc. 2001; 123: 7188
8d Konnick MM, Guzei IA, Stahl SS. J. Am. Chem. Soc. 2004; 126: 10212
8e Yamashita M, Goto K, Kawashima T. J. Am. Chem. Soc. 2005; 127: 7294

9 Ooi T, Ohmatsu K, Maruoka K. J. Am. Chem. Soc. 2007; 129: 2410

Supplementary Material

Supporting Information