Diastereoselective Pd- or Fe-catalyzed cross-couplings at Csp3-centers; stereoselective functionalization of heterocycles

• Applicant: Professor Dr. Paul Knochel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2011 to 2016
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 205678596

• Final Report Year: 2016

Final Report Abstract

In summary we have reported a range of new diastereoselective cobalt-catalyzed cross-couplings with various cycloalkyl halides. The cross-couplings are highly trans-selective and do not require the stereo-control of the starting halide. The reaction being stereo-convergent and the final result is dictated by steric hindrance favoring the trans-products. In the course of this work, a new chromiumcatalyzed arylation with Grignard reagents has been discovered as well as a new Cl/Zn-exchange reaction catalyzed by Co(acac)2. Further investigations on Cr- and Co-catalyzed cross-couplings are currently underway in our laboratories and this research will be a section of a future DFG-research proposal.

Publications

• Org. Lett. 2011, 13, 3174-3177
  L. Melzig, C. R. Diene, C. J. Rohbogner, P. Knochel
  
• Org. Lett. 2014, 16, 5208-5211
  O. M. Kuzmina, P. Knochel
  (See online at https://doi.org/10.1021/ol502623v)
• Org. Lett. 2014, 16, 6500-6503
  J. M. Hammann, A. K. Steib, P. Knochel
  (See online at https://doi.org/10.1021/ol503361m)
• Angew. Chem. Int. Ed. 2015, 54, 4478-4481
  . M. Hammann, D. Haas, P. Knochel
  (See online at https://doi.org/10.1002/anie.201411960)
• Chem. Eur. J. 2015, 21, 8242-8249
  O. M. Kuzmina, A. K. Steib, S. Fernandez, W. Boudot, J. T. Markiewicz, P. Knochel
  (See online at https://doi.org/10.1002/chem.201500747)
• Synthesis 2015, 47, 1461-1468
  J. M. Hammann, D. Haas, A. K. Steib, P. Knochel
  (See online at https://doi.org/10.1055/s-0034-1380407)
• Mild Cobalt-Catalyzed Negishi Cross-Couplings of (Hetero)arylzinc Reagents with (Hetero)aryl Halides. Angew. Chem. Int. Ed. 2016, 55, 3809-3812
  D. Haas, J. M. Hammann, F. H. Lutter, P. Knochel
  (See online at https://doi.org/10.1002/anie.201510665)