This thesis describes the development of titanium catalysed C-N bond forming reactions of alkynes and diazenes. These reactions proceed through a TiIV/II catalytic cycle and a unique diazene cleavage step. Chapter 1 details previous titanium redox reactions for the formation of CX bonds. Chapters 2 and 3 describe the discovery, development, and mechanism of the titanium catalysed [2+2+1] coupling of alkynes and diazenes for the synthesis of multisubsituted pyrroles. Chapter 4 describes the 3-component coupling of alkenes, alkynes, and diazenes in the synthesis of α,β-unsaturated imines and α-(iminomethyl) cyclopropanes. Finally, Chapter 5 describes the development of a benchtop stable catalyst system for a series of titanium catalysed C-N and C-C bond forming reactions.
University of Minnesota Ph.D. dissertation. September 2018. Major: Chemistry. Advisor: Ian Tonks. 1 computer file (PDF); viii, 261 pages.
Development, Mechanism, and Application of Titanium(II/IV) Catalysed C-N Bond Forming Reactions.
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