The challenge of achieving selective and predictable functionalizations at C-H bonds with complex poly(hetero)aromatic substrates was addressed by two different approaches. Site-selectivity can be obtained by applying various reaction conditions that are (hetero)arene specific to substrates that contain indoles, pyridine N-oxide, and polyfluorinated benzenes. An experimental classification of electron-rich heteroarenes based on their reactivity toward palladium-catalyzed C-H functionalization was established, the result of which correlated well with the order of reactivity predicted by the DFT-calculated concerted metalation-deprotonation (CMD) pathway. Model substrates containing two reactive heteroarenes were then reacted under general reaction conditions to demonstrate the applicability this reactivity chart in predicting the regioselectivity of the palladium-catalyzed direct arylation and benzylation reactions.

No abstract

The author has granted a nonexclusive license allowing Library and Archives Canada to reproduce, publish, archive, preserve, conserve, communicate to the public by telecommunication or on the Internet, loan, distribute and sell theses worldwide, for commercial or noncommercial purposes, in microform, paper, electronic and/or any other formats. L'auteur a accorde une licence non exclusive permettant a la Bibliotheque et Archives Canada de reproduire, publier, archiver, sauvegarder, conserver, transmettre au public par telecommunication ou par I'lntemet, preter, distribuer et vendre des theses partout dans le monde, a des fins commerciales ou autres, sur support microforme, papier, electronique et/ou autres formats. Bien que ces formulaires aient inclus dans la pagination, il n'y aura aucun contenu manquant.

Graphical abstract

A large abdominal mass containing numerous cysticerci identified as those of Taenia crassiceps (=Cysticercus longicollis) was found in the pelvic region of the abdominal cavity of a severely constipated and emaciated red fox ( Vulpes vulpes ) in Prince Edward Island, Canada. Cysticercosis has not previously been reported in a wild canid in North America.