Subscribe to RSS
DOI: 10.1055/s-0028-1087418
Preparation and Catalytic Performance of Novel Dimeric Tetranuclear Zinc Complexes in Hydroamination of Alkenes at Room Temperature
Publication History
Publication Date:
27 November 2008 (online)
![](https://www.thieme-connect.de/media/synlett/200820/lookinside/thumbnails/10.1055-s-0028-1087418-1.jpg)
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 for this article is available online:
- Supporting Information
-
1a
Dochnahl M. PhD Thesis Technische Universität Berlin; Germany: 2007. -
1b
Horrillo-Martínez P.Hultzsch KC.Gil A.Branchadell V. Eur. J. Org. Chem. 2007, 3311 -
1c
Datta S.Roesky PW.Blechert S. Organometallics 2007, 26: 4392 -
1d
Wood MC.Leitch DC.Yeung CS.Kozak JA.Schafer LL. Angew. Chem. 2007, 119: 358 -
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 -
1f
Zhang Z.Bender CF.Widenhoefer RA. Org. Lett. 2007, 9: 2887 -
1g
Yu X.Marks TJ. Organometallics 2007, 26: 365 -
1h
Meyer N.Löhnwitz K.Zulys A.Roesky PW.Dochnahl M.Blechert S. Organometallics 2006, 25: 3730 -
1i
Dochnahl M.Pissarek J.-W.Blechert S.Löhnwitz K.Roesky PW. Chem. Commun. 2006, 3405 -
1j
Michael FE.Cochran BM. J. Am. Chem. Soc. 2006, 128: 4246 -
1k
Bender CF.Widenhoefer RA. Org. Lett. 2006, 8: 5303 -
1l
Komeyama K.Morimoto T.Takaki K. Angew. Chem. 2006, 45: 2938 -
1m
Zhang J.Yang C.-G.He C. J. Am. Chem. Soc. 2006, 128: 1798 -
1n
Meyer N.Zulys A.Roesky PW. Organometallics 2006, 25: 4179 -
1o
Riegert D.Collin J.Meddour A.Schulz E.Trifonov A. J. Org. Chem. 2006, 71: 2514 -
1p
Zulys A.Dochnahl M.Hollmann D.Löhnwitz K.Herrmann J.-S.Roesky PW.Blechert S. Angew. Chem. 2005, 44: 7794 -
1q
Karshtedt D.Bell AT.Tilley TD. J. Am. Chem. Soc. 2005, 127: 12640 -
1r
Kim JY.Livinghouse T. Org. Lett. 2005, 7: 1737 -
1s
Bexrud JA.Beard JD.Leitch DC.Schafer LL. Org. Lett. 2005, 7: 1959 -
1t
Kim JY.Livinghouse T. Org. Lett. 2005, 7: 4391 -
1u
Crimmin MR.Casely IJ.Hill MS. J. Am. Chem. Soc. 2005, 127: 2042 -
1v
Lauterwasser F.Hayes PG.Bräse S.Piers WE.Schafer LL. Organometallics 2004, 23: 2234 -
1w
Gribkov DV.Hultzsch KC. Angew. Chem. 2004, 43: 5542 -
1x
Ryu J.-S.Marks TJ.McDonald FE. J. Org. Chem. 2004, 69: 1038 -
1y
Hong S.Marks TJ. Acc. Chem. Res. 2004, 37: 673 -
1z
Hong S.Kawaoka AM.Marks TJ. J. Am. Chem. Soc. 2003, 125: 15878 -
2a
Luo G.Chen L.Civiello R.Dubowchik GM. Tetrahedron Lett. 2008, 49: 296 -
2b
Gong H.Sinisi R.Gagné MR. J. Am. Chem. Soc. 2007, 129: 1908 -
2c
Melzig L.Gavryushin A.Knochel P. Org. Lett. 2007, 9: 5529 -
2d
Huang Z.Negishi E. J. Am. Chem. Soc. 2007, 129: 14788 -
2e
Pilz MF.Limberg C.Lazarov BB.Hultzsch KC.Ziemer B. Organometallics 2007, 26: 3668 -
2f
Paradowska J.Stodulski M.Mlynarski J. Adv. Synth. Catal. 2007, 349: 1041 -
2g
Yan G.Wu Y.Lin W.Zhang X. Tetrahedron: Asymmetry 2007, 18: 2643 -
2h
Tanyeli C.Odabaº S.Erdem M.Çakir E.Keskin E. Tetrahedron: Asymmetry 2007, 18: 2349 -
2i
El-Shehawy AA. Tetrahedron 2007, 63: 5490 -
2j
Du H.Long J.Shi Y. Org. Lett. 2006, 8: 2827 -
2k
Jankowska J.Mlynarski J. J. Org. Chem. 2006, 71: 1317 -
2l
Bok T.Yun H.Lee BY. Inorg. Chem. 2006, 45: 4228 -
2m
Xiao Y.Wang Z.Ding K. Chem. Eur. J. 2005, 11: 3668 -
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 -
2o
Trost BM.Shin S.Sclafani JA. J. Am. Chem. Soc. 2005, 127: 8602 -
2p
Fernandez-Lopez R.Kofoed J.Machuqueiro M.Darbre T. Eur. J. Org. Chem. 2005, 5268 -
2q
Cozzi PG.Rudolph J.Bolm C.Norrby P.Tomasini C. J. Org. Chem. 2005, 70: 5733 -
2r
Aggarwal VK.Fang GY.Meek G. Org. Lett. 2003, 5: 4417 -
2s
Ross NA.Bartsch RA. J. Org. Chem. 2003, 68: 360 -
2t
Moore DR.Cheng M.Lobkovsky EB.Coates GW. J. Am. Chem. Soc. 2003, 125: 11911 -
2u
Nakano K.Nozaki K.Hiyama T. J. Am. Chem. Soc. 2003, 125: 5501 -
2v
Trost BM.Silcoff ER.Ito H. Org. Lett. 2001, 3: 2497 -
2w
Durant A.Delplancke JL.Libert V.Reisse J. Eur. J. Org. Chem. 1999, 2845 -
2x
Bieber LW.Malvestiti I.Storch EC. J. Org. Chem. 1997, 62: 906 -
2y
Yeh S.-M.Huang L.-H.Luh T.-Y. J. Org. Chem. 1996, 61: 3906 -
2z
Chou T.Tseng H.-J. Tetrahedron Lett. 1995, 36: 7105 - 3
Shibasaki M.Yamamoto Y. In Multimetallic Catalysts in Organic Synthesis Wiley-VCH; Weinheim: 2004. - 4
Nozoe T.Okai H.Wakabayashi H.Ishikawa S. Bull. Chem. Soc. Jpn. 1989, 62: 2307 -
5a
Crous R.Datt M.Foster D.Bennie L.Steencamp C.Huyser J.Kirsten L.Steyl G.Roodt A. Dalton Trans. 2005, 1108 -
5b
Houte H.Valnot J.-Y.Piettre SR. Tetrahedron Lett. 2002, 43: 9217 -
5c
Piettre SR.Ganzhorn A.Hoflack J.Islam K.Hornsperger JM. J. Am. Chem. Soc. 1997, 119: 3201 -
5d
Nozoe T.Takase K.Yasunami M. Bull. Chem. Soc. Jpn. 1971, 44: 2218 -
5e
Nozoe T.Ryu S.Toda T. Bull. Chem. Soc. Jpn. 1968, 41: 2978 -
5f
Doering W.Knox LH. J. Am. Chem. Soc. 1952, 74: 5683 - 7
Kirby A. J. Adv. Phys. Org. Chem. 1980, 17: 183
References and Notes
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) ų, 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) ų, 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).