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Alternatives to Bu 3 SnH in Radical Cyclisations: Copper Mediated 4-Exo and 5-Endo Radical Polar-Crossover Reactions Dr. Andrew Clark Associate Professor.

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Presentation on theme: "Alternatives to Bu 3 SnH in Radical Cyclisations: Copper Mediated 4-Exo and 5-Endo Radical Polar-Crossover Reactions Dr. Andrew Clark Associate Professor."— Presentation transcript:

1 Alternatives to Bu 3 SnH in Radical Cyclisations: Copper Mediated 4-Exo and 5-Endo Radical Polar-Crossover Reactions Dr. Andrew Clark Associate Professor of Synthetic Chemistry Director Of Undergraduate Studies University of Warwick +44 24 76523242 a.j.clark@warwick.ac.uk New Trends in Applied Chemistry, Ovidius University of Constanta, 2012

2 Stoichiometric Reductive Cyclisation Toxic Reagents Purification Issues Relatively expensive (10g, £25) Classical Radical Cyclisation

3 Atom Transfer Radical Cyclisation

4 A. J. Clark, J. V. Geden, and S. Thom. J. Org. Chem., 2006, 71, 1471

5 A. J. Clark, J. V. Geden, S. Thom, and P. Wilson, J. Org. Chem., 2007, 72, 5923

6 5-Endo Cyclisations Radical-polar crossover reaction

7

8 Unprecedented radical-polar-carbene triple crossover reaction

9 Improving catalysis

10 A. J. Clark, P. Wilson. Tetrahedron Letts., 2008, 49, 4848 Addition of AIBN

11 Applications

12 Other reducing agents

13 Acknowledgements PhD students Gary Battle John McDonagh Joanna Geden Paul Wilson Post Doctoral Alana Collis Funding Aventis Lilly Research Centre AstraZeneca Engineering and Physical Sciences Research Council EPSRC New Materials and Analytical extension £24M, 5 storeys, 4656 sq m. opened November 2011 New synthetic lab Opened Nov 2010 by Prof. Grubbs New 700 MHz NMR New teaching lab, October 2012!


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