Cationic Late-Transition-Metal
Complexes Catalyze the Ring Opening of Aziridines with
Amines

Alex Marti; Saravanan Peruncheralathan; Christoph Schneider

doi:10.1055/s-0031-1289611

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Synthesis 2012(1): 27-36
DOI: 10.1055/s-0031-1289611

FEATUREARTICLE

Cationic Late-Transition-Metal Complexes Catalyze the Ring Opening of Aziridines with Amines

Alex Marti, Saravanan Peruncheralathan^¹, Christoph Schneider*
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: schneider@chemie.uni-leipzig.de;

Further Information

Publication History

Received 20 September 2011
Publication Date:
18 November 2011 (online)

Abstract
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Abstract

Cationic palladium and nickel complexes have been found to catalyze the ring-opening of meso-N-aryl aziridines with anilines very efficiently and furnish valuable 1,2-diamines in typically excellent yields. The active catalysts were generated in situ from the corresponding metal dichloride bis(triphenylphosphine) complexes through chloride abstraction with a silver salt. This new protocol is applicable across a broad substrate range with both cyclic as well as acyclic aziridines. In addition, cationic gold-phosphine complexes proved to be highly reactive as well as delivering products in comparable rates and yields.

Key words

aziridine - catalysis - 1,2-diamine - nickel - palladium

References

Selected reviews:
2a Schneider C. Synthesis 2006, 3919

Google Scholar
2b Pastor IM. Yus M. Curr. Org. Chem. 2005, 9: 1

Google Scholar
2c Jacobsen EN. Wu MH. Comprehensive Asymmetric Catalysis Vol. 2: Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999. p.649

Google Scholar
Selected reviews:
3a Schneider C. Angew. Chem. Int. Ed. 2009, 48: 2082

Google Scholar
3b Yudin AK. Aziridines and Epoxides in Organic Synthesis Wiley-VCH; Weinheim: 2006.

Google Scholar
3c Pineschi M. Eur. J. Org. Chem. 2006, 4979

Google Scholar
3d Hu XE. Tetrahedron 2004, 60: 2701

Google Scholar
3e McCoull W. Davis FA. Synthesis 2000, 1347

Google Scholar
For selected catalytic processes, see:
4a Hong D. Lin X. Zhu Y. Lei M. Wang Y. Org. Lett. 2009, 11: 5678

Google Scholar
4b Bisai A. Bhanu Prasad BA. Singh VK. Tetrahedron Lett. 2005, 46: 7935

Google Scholar
4c Wu J. Sun X. Li Y. Eur. J. Org. Chem. 2005, 4271

Google Scholar
4d Watson IDG. Yudin AK.
J. Org. Chem. 2003, 68: 5160

Google Scholar
4e Swamy NR. Venkateswarlu Y. Synth. Commun. 2003, 33: 547

Google Scholar
4f Yadav JS. Reddy BVS. Rao KV. Raj KS. Prasad AR. Synthesis 2002, 1061

Google Scholar
4g Cossy J. Bellosta V. Alauze V. Desmurs JR. Synthesis 2002, 2211

Google Scholar
4h Hou X.-L. Fan R.-H. Dai L.-X. J. Org. Chem. 2002, 67: 5295

Google Scholar
4i Chandrasekhar M. Sekar G. Singh VK. Tetrahedron Lett. 2000, 41: 10079

Google Scholar
4j Sekar G. Singh VK. J. Org. Chem. 1999, 64: 2537

Google Scholar
4k Meguro M. Asao N. Yamamoto Y. Tetrahedron Lett. 1994, 35: 7395

Google Scholar
For selected catalytic processes, see:
5a Bhadra S. Adak L. Samanta S. Maidul Islam AKM. Mukherjee M. Ranu BC. J. Org. Chem. 2010, 75: 8533

Google Scholar
5b Bera M. Roy S. J. Org. Chem. 2009, 74: 8814

Google Scholar
5c Bhanu Prasad BA. Sanghi R. Singh VK. Tetrahedron 2002, 58: 7355

Google Scholar
5d Hou X.-L. Fan R.-H. Dai L.-X. J. Org. Chem. 2002, 67: 5295

Google Scholar
5e Bhanu Prasad BA. Sekar G. Singh VK. Tetrahedron Lett. 2000, 41: 4677

Google Scholar
For selected catalytic processes, see:
6a Zhang Y. Wee Kee C. Lee R. Fu X. Soh JYT. Loh EMF. Huang KW. Tan CH. Chem. Commun. 2011, 47: 3897

Google Scholar
6b Zeng F. Alper H. Org. Lett. 2010, 12: 5567

Google Scholar
6c Yadav JS. Reddy BVS. Baishya G. Venkatram Reddy P. Narsaiah AV. Catal. Commun. 2006, 7: 807

Google Scholar
6d Wu J. Sun X. Li Y. Eur. J. Org. Chem. 2005, 4271

Google Scholar
6e Yadav JS. Subba Reddy BV. Baishya G. Reddy PV. Harshavardhan SJ. Synthesis 2004, 1854

Google Scholar
6f Hou X.-L. Fan R.-H. Dai L.-X. J. Org. Chem. 2002, 67: 5295

Google Scholar
6g Wu J. Hou X.-L. Dai L.-X. J. Chem. Soc., Perkin Trans. 1 2001, 1314

Google Scholar
7 Li Z. Fernandez M. Jacobsen EN. Org. Lett. 1999, 1: 1611

Google Scholar
8a Yabu K. Masumoto S. Yamasaki S. Hamashima Y. Kanai M. Du W. Curran DP. Shibasaki M. J. Am. Chem. Soc. 2001, 123: 9908

Google Scholar
8b Mita T. Fujimori I. Wada R. Wen J. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2005, 127: 11252

Google Scholar
8c Fukuta Y. Mita T. Fukuda N. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2006, 128: 6312

Google Scholar
8d Fujimori I. Mita T. Maki K. Shiro M. Sato A. Furusho S. Kanai M. Shibasaki M. J. Am. Chem. Soc. 2006, 128: 16438

Google Scholar
8e Xu Y. Lin L. Kanai M. Matsunaga S. Shibasaki M. J. Am. Chem. Soc. 2011, 133: 5791

Google Scholar
9a Arai K. Lucarini S. Salter MS. Ohta K. Yamashita Y. Kobayashi S. J. Am. Chem. Soc. 2007, 129: 8103

Google Scholar
9b Yu R. Yamashita Y. Kobayashi S. Adv. Synth. Catal. 2009, 351: 147

Google Scholar
9c Seki K. Yu R. Yamazaki Y. Yamashita Y. Kobayashi S. Chem. Commun. 2009, 5722

Google Scholar
10a Wu B. Gallucci JC. Parquette JR. RajanBabu TV. Angew. Chem. Int. Ed. 2009, 48: 1126

Google Scholar
10b Wu B. Parquette JR. RajanBabu TV. Science 2009, 326: 1662

Google Scholar
11a Rowland EB. Rowland GB. Rivera-Otero E. Antilla JC. J. Am. Chem. Soc. 2007, 129: 12084

Google Scholar
11b Larson SE. Baso JC. Li G. Antilla JC. Org. Lett. 2009, 11: 5186

Google Scholar
12a Della Sala G. Lattanzi A. Org. Lett. 2009, 11: 3330

Google Scholar
12b Lattanzi A. Della Sala G. Eur. J. Org. Chem. 2009, 1845

Google Scholar
13a Luo Z.-B. Hou X.-L. Dai L.-X. Tetrahedron: Asymmetry 2007, 18: 443

Google Scholar
13b Wang Z. Sun X. Ye S. Wang W. Wang B. Wu J. Tetrahedron: Asymmetry 2008, 19: 964

Google Scholar
14a Slaman SM. Schwab RS. Alberto EE. Vargas J. Dornelles L. Rodrigues OED. Braga AL. Synlett 2011, 69

Google Scholar
14b Ghorai MK. Tiwari DP. J. Org. Chem. 2010, 75: 6173

Google Scholar
14c Yadav LDS. Rai VK. Singh S. Singh P. Tetrahedron Lett. 2010, 51: 1657

Google Scholar
15 Peruncheralathan S. Teller H. Schneider C. Angew. Chem. Int. Ed. 2009, 48: 4849

Google Scholar
16a Peruncheralathan S. Henze M. Schneider C. Synlett 2007, 2289

Google Scholar
16b Marti A. Richter L. Schneider C. Synlett 2011, 2513

Google Scholar
17 Peruncheralathan S. Henze M. Schneider C. Tetrahedron Lett. 2007, 48: 6743

Google Scholar
Silver salts are known to be capable of abstracting chloride anions of transition-metal complexes resulting in cationic metal complexes, see, e.g.:
18a Evans DA. Murry JA. Von Matt P. Norcross RD. Miller SJ. Angew. Chem., Int. Ed. Engl. 1995, 34: 798.

Google Scholar
18b Usuda H. Kuramochi A. Kanai M. Shibasaki M. Org. Lett. 2004, 6: 4387

Google Scholar
18c Cochran BM. Michael FE. Org. Lett. 2008, 10: 329

Google Scholar

1

Current address: National Institute of Science Education and Research, Bhubaneswar 751 005, India.