Date of Award

2016

Publisher

North Dakota State University

Document Type

Thesis

Degree Awarded

Master of Science (MS)

Department

Chemistry and Biochemistry

College

Science and Mathematics

Faculty Advisor

Zhao, Pinjing

Description

Amines are valuable targets for synthesis in contexts of both research and industrial applications. This work proposes two atom-economical methods—hydroamination (HAM) and hydroimination (HIM)—as C-N bond formation strategies. A nickel-(N-heterocyclic carbene) catalyst system was developed to carry out HAM of internal, unactivated alkynes with aryl amines and cyclic secondary amines. It was demonstrated that the Ni-NHC catalyst was capable of promoting both HAM at room temperature and transfer hydrogenation to produce α-branched aryl amines. These two procedures were performed by the same catalyst to demonstrate an elegant 1-pot, multi-transformation protocol. Separately, optimization of a Rh-HIM catalyst system for the combination of monosubstituted allenes and aromatic N-H-ketimine was carried out to favor high conversion of substrates to the linear HIM product rather than [3+2] annulation. Both HAM and HIM C-N bond formation methods were found to be successful and capable of good conversion and selectivity for their respective products.

Rights

NDSU Policy 190.6.2

Rights Link

https://www.ndsu.edu/fileadmin/policy/190.pdf

Handle Identifier

https://hdl.handle.net/10365/28036

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