Synthesis of Amino-Functionalized 2,2′-Bipyridines

Marko Hapke; Holger Staats; Ivonne Wallmann; Arne Lützen

doi:10.1055/s-2007-983824

PAPER

Synthesis of Amino-Functionalized 2,2′-Bipyridines

Marko Hapke^b, Holger Staats^a, Ivonne Wallmann^a, Arne Lützen*^a
^a Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany
^b Leibniz-Institut für Katalyse e.V., Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock, Germany
Fax: +49(228)739608; e-Mail: arne.luetzen@uni-bonn.de;

Abstract

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Abstract

Amino-functionalized 2,2′-bipyridines are versatile building blocks for the synthesis of sophisticated chelating ligands with the 2,2′-bipyridine core. The 4-, 5-, and 6-substituted 2-chloro- and 2-bromopyridine building blocks were prepared and coupled to symmetrically and non-symmetrically diamino-functionalized compounds by homo- and cross-coupling procedures. Further transformations were carried out to demonstrate the synthetic versatility of these compounds and the employed procedures.

Key words

cross-coupling reactions - bipyridine - palladium - protecting group - amines

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References

1 Kaes C. Katz A. Hosseini MW. Chem. Rev. 2000, 100: 3553

2 For the synthetic introduction of the bipyridine core in the synthesis of caerulomycin C, see: Sammakia T. Stangeland EL. Whitcomb MC. In Strategies and Tactics in Organic Synthesis Vol. 6: Harmata M. Elsevier; New York: 2005. p.415

3 Newkome GR. Petri AK. Holder E. Schubert US. Eur. J. Org. Chem. 2004, 235

4a Lützen A. Hapke M. Eur. J. Org. Chem. 2002, 2292

4b Lützen A. Hapke M. Staats H. Bunzen J. Eur. J. Org. Chem. 2003, 3948

4c Kiehne U. Bunzen J. Staats H. Lützen A. Synthesis 2007, 1061

5 Modern Amination Methods Ricci A. Wiley-VCH; Weinheim: 2000.

Examples:

6a Whittle CP. J. Heterocycl. Chem. 1977, 14: 191

6b Newkome GR. Gross J. Patri AK. J. Org. Chem. 1997, 62: 3013

6c Zhang B. Breslow R. J. Am. Chem. Soc. 1997, 119: 1676

6d Thibault ME. Luska KL. Schlaf M. Synthesis 2007, 791

7 Albrecht M. Janser I. Lützen A. Hapke M. Fröhlich R. Weis P. Chem. Eur. J. 2005, 11: 5742

Some recent examples for the use of LiCl as an additive in organometallic mediated reactions:

8a Krasovskiy A. Knochel P. Angew. Chem. Int. Ed. 2004, 43: 3333 ; Angew. Chem. 2004, 116, 3396

8b Krasovskiy A. Straub B. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 159 ; Angew. Chem. 2006, 118, 165

8c Krasovskiy A. Krasovskaya V. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 2958 ; Angew. Chem. 2006, 118, 3024

8d Krasovskiy A. Tishkov A. del Amo V. Mayr H. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 5010 ; Angew. Chem. 2006, 118, 5132

8e Krasovskiy A. Malakhov V. Gavryushin A. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 6040 ; Angew. Chem. 2006, 118, 6186

8f del Amo V. Dubbaka SR. Krasovskiy A. Knochel P. Angew. Chem. Int. Ed. 2006, 45: 7838 ; Angew. Chem. 2006, 118, 8002

8g Korn TB. Scahde MA. Cheemala MN. Wirth S. Guevara SA. Cahiez G. Knochel P. Synthesis 2006, 3547

8h Kloetzing RJ. Krasovskiy A. Knochel P. Chem. Eur. J. 2007, 13: 215

9 Iyoda M. Otsuka H. Sato K. Nisato N. Oda M. Bull. Chem. Soc. Jpn. 1990, 63: 80

Examples:

10a Janiak C. Deblon S. Wu H.-P. Kolm MJ. Klufers P. Piotrowski H. Mayer P. Eur. J. Inorg. Chem. 1999, 1507

10b Devic T. Avarvari N. Batail P. Chem. Eur. J. 2004, 10: 3697

10c Ishida H. Kyakuno M. Oishi S. Biopolymers 2004, 76: 69

11 General overview: Schelhaas M. Waldmann H. Angew. Chem., Int. Ed. Engl. 1996, 35: 2056 ; Angew. Chem. 1996, 108, 2192

12 Bräse S. Acc. Chem. Res. 2004, 37: 805

13 Conditions: Barbero M. Degani I. Diulgheroff N. Dughera S. Fochi R. Synthesis 2001, 2180

14 Suffert J. J. Org. Chem. 1989, 54: 509

15 Dai C. Fu GC. J. Am. Chem. Soc. 2001, 123: 2719

16 Brandsma L. Vasilevsky SF. Verkruijsse HD. Application of Transition Metal Catalysts in Organic Synthesis Springer Verlag; Berlin: 1999. 2: