Catalytic Methods for Formation of Carbon-Nitrogen Bonds

Project Details

Our research in this area seeks to uncover fundamentally new organometallic chemistry that will be the foundation of new catalytic transformations for organic synthesis. Many groups are developing catalysts and transformations that have enabled new synthetic routes to organic products. However, the work on new methods has far outpaced mechanistic studies, which are key to understanding reaction pathways and discovering new reactivity. Thus, we have sought to identify new stoichiometric transformations of organometallic compounds, new catalytic reactions based on these transformations, and new catalytic reactions that occur with unique selectivities that have the potential to develop into valuable methodology.

The collaborative nature of a CENTC program allows us to approach the challenge of carbon–nitrogen bond formation from multiple angles simultaneously. We are evaluating catalysts based on both late and early metals for the formation of arylamine derivatives by radical and non-radical pathways, as well as seeking new organometallic complexes that undergo reductive elimination by both concerted pathways and by nucleophilic attack on a coordinated benzyl or alkyl group. This multi-faceted approach has led to a series of new catalytic reactions and new elementary organometallic reactions leading to these catalytic reactions.

Senior Investigators 

Palladium-Catalyzed Amination of Arenes

Recent Publications and Patents

  • Shrestha, R,; Muhkerjee, P.; Tan, Y.; Litman, Z. C.; Hartwig, J. F. "Sterically Controlled, Palladium-Catalyzed Intermolecular Amination of Arenes", J. Am. Chem. Soc., 2013, 135, 8480-8483. (DOI: 10.1021/ja4032677)
  • Hanley, P. S.; Marquard, S. L.; Cundari, T. R.; Hartwig, J. F. "Reductive Elimination of Alkylamines from Low-Valent, Alkylpalladium(II) Amido Complexes", J. Am. Chem. Soc., 2012, 134 , 15281-15284. (DOI: 10.1021/ja307558x)
  • Marquard, S. L.; Hartwig, J. F. "C(sp3)-O Bond-Forming Reductive Elimination of Ethers from Bisphosphine-Ligated Benzylpalladium(II) Aryloxide Complexes" Angew. Chem. Int. Ed. Eng., 2011, 50, 7119-7123. (DOI: 10.1002/anie.201101088)
  • Kovach, J.; Peralta, M.; Brennessel, W. W.; Jones, W. D. "Synthesis and X-ray Crystallographic Characterization of Substituted Aryl Imines", J. Mol. Struct., 2011, 992, 33-38. (DOI: 10.1016/j.molstruc.2011.02.027)
  • Tan, Y.; Hartwig, J. F., "Palladium-Catalyzed Amination of Aromatic C-H Bonds with Oxime Esters", J. Am. Chem. Soc. , 2010, 132, 3676-3677. (DOI:10.1021/ja100676r)

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This work was supported by NSF under the CCI Center for Enabling New Technologies Through Catalysis, CHE-1205189. Any opinions, findings, and conclusions or recommendations expressed here are those of the authors and do not necessarily reflect the views of the National Science Foundation (NSF).

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