Preparation and Catalytic Performance
of Novel Dimeric Tetranuclear Zinc Complexes in Hydroamination of
Alkenes at Room Temperature

Mustafa Biyikal; Karolin Löhnwitz; Peter W. Roesky; Siegfried Blechert

doi:10.1055/s-0028-1087418

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2008(20): 3106-3110
DOI: 10.1055/s-0028-1087418

LETTER

Preparation and Catalytic Performance of Novel Dimeric Tetranuclear Zinc Complexes in Hydroamination of Alkenes at Room Temperature

Mustafa Biyikal, Karolin Löhnwitz, Peter W. Roesky*^a, Siegfried Blechert*^b
^a Institut für Anorganische Chemie, Universität Karlsruhe, Engesserstr. 15, 76128 Karlsruhe, Germany
Fax: +49(721)6084854; e-Mail: roesky@chemie.uni-karlsruhe.de;
^b Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 135, 10623 Berlin, Germany
Fax: +49(30)31423619; e-Mail: blechert@chem.tu-berlin.de;

Further Information

Publication History

Received 10 August 2008
Publication Date:
27 November 2008 (online)

Abstract
Full Text
References
Supplementary Material

Permissions and Reprints All articles of this category

Abstract

The synthesis of two novel dimeric tetranuclear zinc complexes has been described. The application of these complexes in hydroamination of unactivated alkenes showed at room temperature high catalytic activity.

Key words

alkenes - heterocycles - hydroamination - tetranuclear - zinc

Supporting Information

References and Notes

1a Dochnahl M. PhD Thesis Technische Universität Berlin; Germany: 2007.

Google Scholar
1b Horrillo-Martínez P. Hultzsch KC. Gil A. Branchadell V. Eur. J. Org. Chem. 2007, 3311

Google Scholar
1c Datta S. Roesky PW. Blechert S. Organometallics 2007, 26: 4392

Google Scholar
1d Wood MC. Leitch DC. Yeung CS. Kozak JA. Schafer LL. Angew. Chem. 2007, 119: 358

Google Scholar
1e Dochnahl M. Löhnwitz K. Pissarek J.-W. Biyikal M. Schulz SR. Schön S. Meyer N. Roesky PW. Blechert S. Chem. Eur. J. 2007, 13: 6654

Google Scholar
1f Zhang Z. Bender CF. Widenhoefer RA. Org. Lett. 2007, 9: 2887

Google Scholar
1g Yu X. Marks TJ. Organometallics 2007, 26: 365

Google Scholar
1h Meyer N. Löhnwitz K. Zulys A. Roesky PW. Dochnahl M. Blechert S. Organometallics 2006, 25: 3730

Google Scholar
1i Dochnahl M. Pissarek J.-W. Blechert S. Löhnwitz K. Roesky PW. Chem. Commun. 2006, 3405

Google Scholar
1j Michael FE. Cochran BM. J. Am. Chem. Soc. 2006, 128: 4246

Google Scholar
1k Bender CF. Widenhoefer RA. Org. Lett. 2006, 8: 5303

Google Scholar
1l Komeyama K. Morimoto T. Takaki K. Angew. Chem. 2006, 45: 2938

Google Scholar
1m Zhang J. Yang C.-G. He C. J. Am. Chem. Soc. 2006, 128: 1798

Google Scholar
1n Meyer N. Zulys A. Roesky PW. Organometallics 2006, 25: 4179

Google Scholar
1o Riegert D. Collin J. Meddour A. Schulz E. Trifonov A. J. Org. Chem. 2006, 71: 2514

Google Scholar
1p Zulys A. Dochnahl M. Hollmann D. Löhnwitz K. Herrmann J.-S. Roesky PW. Blechert S. Angew. Chem. 2005, 44: 7794

Google Scholar
1q Karshtedt D. Bell AT. Tilley TD. J. Am. Chem. Soc. 2005, 127: 12640

Google Scholar
1r Kim JY. Livinghouse T. Org. Lett. 2005, 7: 1737

Google Scholar
1s Bexrud JA. Beard JD. Leitch DC. Schafer LL. Org. Lett. 2005, 7: 1959

Google Scholar
1t Kim JY. Livinghouse T. Org. Lett. 2005, 7: 4391

Google Scholar
1u Crimmin MR. Casely IJ. Hill MS. J. Am. Chem. Soc. 2005, 127: 2042

Google Scholar
1v Lauterwasser F. Hayes PG. Bräse S. Piers WE. Schafer LL. Organometallics 2004, 23: 2234

Google Scholar
1w Gribkov DV. Hultzsch KC. Angew. Chem. 2004, 43: 5542

Google Scholar
1x Ryu J.-S. Marks TJ. McDonald FE. J. Org. Chem. 2004, 69: 1038

Google Scholar
1y Hong S. Marks TJ. Acc. Chem. Res. 2004, 37: 673

Google Scholar
1z Hong S. Kawaoka AM. Marks TJ. J. Am. Chem. Soc. 2003, 125: 15878

Google Scholar
2a Luo G. Chen L. Civiello R. Dubowchik GM. Tetrahedron Lett. 2008, 49: 296

Google Scholar
2b Gong H. Sinisi R. Gagné MR. J. Am. Chem. Soc. 2007, 129: 1908

Google Scholar
2c Melzig L. Gavryushin A. Knochel P. Org. Lett. 2007, 9: 5529

Google Scholar
2d Huang Z. Negishi E. J. Am. Chem. Soc. 2007, 129: 14788

Google Scholar
2e Pilz MF. Limberg C. Lazarov BB. Hultzsch KC. Ziemer B. Organometallics 2007, 26: 3668

Google Scholar
2f Paradowska J. Stodulski M. Mlynarski J. Adv. Synth. Catal. 2007, 349: 1041

Google Scholar
2g Yan G. Wu Y. Lin W. Zhang X. Tetrahedron: Asymmetry 2007, 18: 2643

Google Scholar
2h Tanyeli C. Odabaº S. Erdem M. Çakir E. Keskin E. Tetrahedron: Asymmetry 2007, 18: 2349

Google Scholar
2i El-Shehawy AA. Tetrahedron 2007, 63: 5490

Google Scholar
2j Du H. Long J. Shi Y. Org. Lett. 2006, 8: 2827

Google Scholar
2k Jankowska J. Mlynarski J. J. Org. Chem. 2006, 71: 1317

Google Scholar
2l Bok T. Yun H. Lee BY. Inorg. Chem. 2006, 45: 4228

Google Scholar
2m Xiao Y. Wang Z. Ding K. Chem. Eur. J. 2005, 11: 3668

Google Scholar
2n Lee BY. Kwon HY. Lee SY. Na SJ. Han S. Yun H. Lee H. Park Y.-W. J. Am. Chem. Soc. 2005, 127: 3031

Google Scholar
2o Trost BM. Shin S. Sclafani JA. J. Am. Chem. Soc. 2005, 127: 8602

Google Scholar
2p Fernandez-Lopez R. Kofoed J. Machuqueiro M. Darbre T. Eur. J. Org. Chem. 2005, 5268

Google Scholar
2q Cozzi PG. Rudolph J. Bolm C. Norrby P. Tomasini C. J. Org. Chem. 2005, 70: 5733

Google Scholar
2r Aggarwal VK. Fang GY. Meek G. Org. Lett. 2003, 5: 4417

Google Scholar
2s Ross NA. Bartsch RA. J. Org. Chem. 2003, 68: 360

Google Scholar
2t Moore DR. Cheng M. Lobkovsky EB. Coates GW. J. Am. Chem. Soc. 2003, 125: 11911

Google Scholar
2u Nakano K. Nozaki K. Hiyama T. J. Am. Chem. Soc. 2003, 125: 5501

Google Scholar
2v Trost BM. Silcoff ER. Ito H. Org. Lett. 2001, 3: 2497

Google Scholar
2w Durant A. Delplancke JL. Libert V. Reisse J. Eur. J. Org. Chem. 1999, 2845

Google Scholar
2x Bieber LW. Malvestiti I. Storch EC. J. Org. Chem. 1997, 62: 906

Google Scholar
2y Yeh S.-M. Huang L.-H. Luh T.-Y. J. Org. Chem. 1996, 61: 3906

Google Scholar
2z Chou T. Tseng H.-J. Tetrahedron Lett. 1995, 36: 7105

Google Scholar
3 Shibasaki M. Yamamoto Y. In Multimetallic Catalysts in Organic Synthesis Wiley-VCH; Weinheim: 2004.

Google Scholar
4 Nozoe T. Okai H. Wakabayashi H. Ishikawa S. Bull. Chem. Soc. Jpn. 1989, 62: 2307

Crossref Google Scholar
5a Crous R. Datt M. Foster D. Bennie L. Steencamp C. Huyser J. Kirsten L. Steyl G. Roodt A. Dalton Trans. 2005, 1108

Google Scholar
5b Houte H. Valnot J.-Y. Piettre SR. Tetrahedron Lett. 2002, 43: 9217

Google Scholar
5c Piettre SR. Ganzhorn A. Hoflack J. Islam K. Hornsperger JM. J. Am. Chem. Soc. 1997, 119: 3201

Google Scholar
5d Nozoe T. Takase K. Yasunami M. Bull. Chem. Soc. Jpn. 1971, 44: 2218

Google Scholar
5e Nozoe T. Ryu S. Toda T. Bull. Chem. Soc. Jpn. 1968, 41: 2978

Google Scholar
5f Doering W. Knox LH. J. Am. Chem. Soc. 1952, 74: 5683

Google Scholar
7 Kirby A. J. Adv. Phys. Org. Chem. 1980, 17: 183

Google Scholar

6

Single-Crystal X-ray Diffraction Data of Compound 4
C₃₄H₅₂Br₄N₄O₂Zn₄˙0.5 (toluene) (1175.98): Stoe IPDS 2T, space group C2/c (No. 15) with a = 29.1063 (12) Å, b = 17.2017 (7) Å, c = 22.2739 (9) Å, β = 126.790 (2)˚ at 200 K, Z = 8, V = 8931.0(6) Å^³, ρ = 1.749 g cm^-³, 2θ _max = 50˚, 7865 reflections collected, 6354 unique reflections (R _int = 0.0860). The structure was solved by Patterson methods (SHELXS-97 and SHELXL-97) and refined by full-matrix least-square techniques with I > 2σ(I) to R ₁ = 0.0483 and wR ₂ = 0.1190.
Single-Crystal X-ray Diffraction Data of Compound 9
C₃₄H₅₆N₄O₂Zn₄ (814.31): Oxford Diffraction Xcalibur S Sapphire, space group P6₁ (No. 169) with a = 11.21070 (10) Å, c = 50.8375 (12) Å, at 150 K, Z = 6, V = 5533.25 (15) Å^³, ρ = 1.466 g cm^-³, 2θ _max = 50˚, 41505 reflections collected, 6515 unique reflections (R _int = 0.0898). The structure was solved by Patterson methods (SHELXS-97 and SHELXL-97) and refined by full-matrix least-square techniques with I > 2σ(I) to R ₁ = 0.0605 and wR ₂ = 0.0812.
Positional parameters, hydrogen-atom parameters, thermal parameters, bond lengths and angles have been deposited as Supporting Information; CCDC-689633 (4) and 689634 (9).

Supplementary Material

Supporting Information