Book of Abstracts - Ruhr-Universität Bochum
Book of Abstracts - Ruhr-Universität Bochum Book of Abstracts - Ruhr-Universität Bochum
P-49 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Bioinspired Catalysts With Bifunctional P,N - Ligands in Alkyne – Hydration Anna Louisa Noffke a and Peter C. Kunz *a a Department of Inorganic Chemistry I, Heinrich-Heine-University of Düsseldorf Universitätsstr. 1, D-40225 Düsseldorf, Email: anna-louisa.noffke@uni-duesseldorf.de Addition of water to terminal alkynes is a common path to carbonyl compounds. However, most synthetic strategies suffer from rather intense conditions or low selectivity. In nature, the tungstenoenzyme acetylene hydratase catalyzes the formation of ethanal from acetylene, for example in pelobacter acetylenicus. 1 For higher alkynes, the hydration-reaction can be equally accelerated using transition-metal catalysts with bifuntional ligands. 2 Systems similar to 1 (Fig. 1) perform with high yields and splendit selectivity. 2 Fig. 1 Preparation of a Ru(II)-vinylidene complex and P,N-Ligands used. With ruthenium(II)-complexes of the general formula [(Cp)Ru(L)2Cl] (Cp = cyclopentadienyl) bearing our water-soluble, hemilabile P,N-ligands 3 (Fig. 1), catalytic activity in alkyne-hydration is observed under certain conditions. The first mechanistic steps of this reaction involve formation of vinylidene species which are subsequently aquated. In particular, the special role that is played by H-bonddonating and/or accepting ligand-functionalities within this catalytic process is explored in further detail. References 1. S. Antony and C. A. Bayse, Organometallics 2009, 28, 4938–4944. (b) M. A. Vincent, I. H. Hillier, G. Periyasamy and N. A. Burton, Dalton Trans. 2010, 39, 3816–3822. 3. (a) D. B. Grotjahn, D.A. Lev; J. Am. Chem. Soc. 2004, 126, 12232. (b) D.B. Grotjahn, Dalton Trans. 2008, 6497. 2. (a) P. C. Kunz, M. U. Kassack, A. Hamacher, B. Spingler, Dalton Trans. 2009, 7741-7747. (b) P. C. Kunz, G. J. Reiß, W. Frank, W. Kläui, Eur. J. Inorg. Chem. 2003, 3945-3951. 107
P-50 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum A Tri-organometallic Derivative Containing a PNA Backbone: Synthesis and Antibacterial Activity Malay Patra, a Gilles Gasser, a# Dmytro Bobukhov, b Klaus Merz, a Alexander V. Shtemenko b Julia E. Bandow c and Nils Metzler-Nolte* a a Lehrstuhl für Anorganische Chemie I, Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Gebäude NC 3 Nord, Universitätsstr. 150, 44801 Bochum, Germany; b Department of Inorganic Chemistry, Ukrainian State Chemical Technological University, Gagarin Avenue 8, Dnipropetrovs'k, 49005 Ukraine; c Lehrstuhl für Biologie der Mikroorganismen, Fakultät für Biologie und Biotechnologie, Ruhr-Universität Bochum, Universitätsstr. 150, 44801 Bochum, Germany. # new address: Institute of Inorganic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland. Novel synthetic routes for the incorporation of different organometallic entities into the same biomolecule are highly demanded. With the strive of developing a reaction sequence for the controlled and sequential insertion of distinct organometallics into a PNA oligomer, we have chosen, as a model compound, namely, 2-(N-(2-(2-(9H-fluoren-9-yloxy)acetamido)ethyl)pent-4-ynamido)acetic acid containing both a PNA backbone and an alkyne side-chain and three different organometallics, azidomethyl ferrocene, β-cymantrenoyl-propionic acid and [{N, N-bis((pyridin-2-yl)methyl)prop-2yn-1-amine}Re(CO)3]PF6 – were inserted using click chemistry, amide bond formation and Sonogashira coupling as orthogonal derivatisation methods respectively. Moreover, we discovered, the triorganometallic compound (1) has excellent antibacterial activity against a number of multidrug resistant gram-positive bacterial strains. References 1. M. Patra, G. Gasser, D. Bobukhov, K. Merz, A.V. Shtemenko, N. Metzler-Nolte, Dalton Trans. 2010, DOI: 10.1039/c003598j. 108
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P-49<br />
ISBOMC `10 5.7 – 9.7. 2010 <strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong><br />
Bioinspired Catalysts With Bifunctional P,N - Ligands in Alkyne – Hydration<br />
Anna Louisa N<strong>of</strong>fke a and Peter C. Kunz *a<br />
a Department <strong>of</strong> Inorganic Chemistry I, Heinrich-Heine-University <strong>of</strong> Düsseldorf<br />
<strong>Universität</strong>sstr. 1, D-40225 Düsseldorf, Email: anna-louisa.n<strong>of</strong>fke@uni-duesseldorf.de<br />
Addition <strong>of</strong> water to terminal alkynes is a common path to carbonyl compounds. However, most<br />
synthetic strategies suffer from rather intense conditions or low selectivity. In nature, the<br />
tungstenoenzyme acetylene hydratase catalyzes the formation <strong>of</strong> ethanal from acetylene, for example<br />
in pelobacter acetylenicus. 1 For higher alkynes, the hydration-reaction can be equally accelerated<br />
using transition-metal catalysts with bifuntional ligands. 2 Systems similar to 1 (Fig. 1) perform with<br />
high yields and splendit selectivity. 2<br />
Fig. 1 Preparation <strong>of</strong> a Ru(II)-vinylidene complex and P,N-Ligands used.<br />
With ruthenium(II)-complexes <strong>of</strong> the general formula [(Cp)Ru(L)2Cl] (Cp = cyclopentadienyl) bearing<br />
our water-soluble, hemilabile P,N-ligands 3 (Fig. 1), catalytic activity in alkyne-hydration is observed<br />
under certain conditions. The first mechanistic steps <strong>of</strong> this reaction involve formation <strong>of</strong> vinylidene<br />
species which are subsequently aquated. In particular, the special role that is played by H-bonddonating<br />
and/or accepting ligand-functionalities within this catalytic process is explored in further<br />
detail.<br />
References<br />
1. S. Antony and C. A. Bayse, Organometallics 2009, 28, 4938–4944. (b) M. A. Vincent, I. H. Hillier,<br />
G. Periyasamy and N. A. Burton, Dalton Trans. 2010, 39, 3816–3822.<br />
3. (a) D. B. Grotjahn, D.A. Lev; J. Am. Chem. Soc. 2004, 126, 12232. (b) D.B. Grotjahn, Dalton<br />
Trans. 2008, 6497.<br />
2. (a) P. C. Kunz, M. U. Kassack, A. Hamacher, B. Spingler, Dalton Trans. 2009, 7741-7747. (b) P. C.<br />
Kunz, G. J. Reiß, W. Frank, W. Kläui, Eur. J. Inorg. Chem. 2003, 3945-3951.<br />
107
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