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Investigation of the Steric and Electronic Properties of 3-Iminophosphine Ligands in Chelated Palladium Allyl Complexes for Use in the Regioselective Hydroamination of Allenes

Zingales, Nicholas C.
http://rave.ohiolink.edu/etdc/view?acc_num=toledo1356544579

Abstract Details

2013, Master of Science, University of Toledo, Chemistry.
A series of (3-iminophosphine)allylpalladium triflate complexes varying in both steric and electronic features was isolated and characterized. The propensity of the complexes in this series to regioselectively catalyze the hydroamination of 3-methyl-1,2-butadiene with aryl amines to form solely the kinetic product at room temperature was studied by observing conversion to products via NMR spectroscopy. An understanding of the importance of these 3-iminophosphine ligand features guides the rational design of future catalysts. The 3-iminophosphine ligand composed of di-tert-butyl phosphine, cyclobutene backbone, and tert-butyl imine provided the most active palladium catalyst for this hydroamination when compared to the other complexes in the collection. Larger alicyclic backbone sizes decrease catalytic activity, as does steric hindrance at the imine substituent group. Tertiary aliphatic groups on the phosphorus are necessary for effective catalysis, as primary and secondary aliphatics and aromatic groups also decrease the catalytic activity. Highly basic imine moieties were also shown to decrease catalytic activity.
Joseph Schmidt, PhD (Committee Chair)
Mark Mason, PhD (Committee Member)
Jianglong Zhu, PhD (Committee Member)
82 p.
Chemistry
hydroamination; 3-iminophosphine; palladium; intermolecular, anilines; allenes

Recommended Citations

Citations

  • Zingales, N. C. (2013). Investigation of the Steric and Electronic Properties of 3-Iminophosphine Ligands in Chelated Palladium Allyl Complexes for Use in the Regioselective Hydroamination of Allenes [Master's thesis, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1356544579

    APA Style (7th edition)

  • Zingales, Nicholas. Investigation of the Steric and Electronic Properties of 3-Iminophosphine Ligands in Chelated Palladium Allyl Complexes for Use in the Regioselective Hydroamination of Allenes. 2013. University of Toledo, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1356544579.

    MLA Style (8th edition)

  • Zingales, Nicholas. "Investigation of the Steric and Electronic Properties of 3-Iminophosphine Ligands in Chelated Palladium Allyl Complexes for Use in the Regioselective Hydroamination of Allenes." Master's thesis, University of Toledo, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1356544579

    Chicago Manual of Style (17th edition)

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© 2012, all rights reserved.
This open access ETD is published by University of Toledo and OhioLINK.
Release 3.2.12