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Zirconium Catalyst Follows a Low Energy Pathway for Carbon-Nitrogen Bond Formation

Chemists have synthesized a highly selective and highly efficient zirconium catalyst that makes new carbon-nitrogen bonds by adding a nitrogen-hydrogen bond to a carbon-carbon double bond.  Nitrogen-containing chemicals are important as agrichemicals, pharmaceuticals, and specialty chemicals. These zirconium catalysts are expected to show greater tolerance to other functionality than the well-known and highly sensitive rare earth catalysts.  The new catalysts are more efficient than previously reported zirconium catalysts, promoting the reaction at room temperature. This high activity may be related to its ability to access a new mechanistic pathway that was proposed based on unique kinetic and selectivity observations. In this mechanism, carbon-nitrogen and carbon-hydrogen bond formation occurs in a concerted fashion.

 

K. Manna, S. Xu and A. D. Sadow , "A Highly Enantioselective Zirconium Catalyst for Intramolecular Alkene Hydroamination: Significant Isotope Effects on Rate and Stereoselectivity" Angewandte Chemie, 2011, 50, 1865-1868  

http://onlinelibrary.wiley.com/doi/10.1002/anie.201006163/abstract

Highlight Date: 
Monday, February 21, 2011