Daugulis, Olafs2023-07-092023-07-09August 2012017-07-13https://hdl.handle.net/10657/14957Direct C–H bond functionalization is a useful synthetic method because it allows formation of C–C bonds directly from C–H bonds. However, directed functionalization of C(sp3)-H bonds is relatively rare. In this thesis, a method for palladium catalyzed, pyridinium ylide-directed C(sp3)-H bond aryaltion by aryl iodides has been developed. The reaction employs Pd(OAc)2 catalyst at 5-10 mol % loading and AgOAc or AgO2CCF3 as a halide-removal agent and hexafluoroisopropanol as solvent. A variety of functional groups, such as methoxy, bromo, ether, ester, aldehyde, trifluoromethoxy and fluoro are tolerated. Monoprotected amino acid ligands were found to significantly promote secondary C(sp3)-H bond arylation. Furthermore, we have also demonstrated that 4-pyrrolidinopyridinium ylide is able to activate methylene C(sp3)-H bonds without addition of external ligands. The pyridinium directing group can be easily removed through N-N bond cleavage using zinc or magnesium metals.application/pdfengThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).C-C couplingC-H activationN-aminopyridinium ylidePalladium2023-07-09Thesisborn digital