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.

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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.

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Ring closure reactions O 0130Hydrazides as Tunable Reagents for Alkene Hydroamination and Aminocarbonylation. -N-Benzoyl hydrazides undergo Cope-type intramolecular hydroaminations to give five-, six-, and seven-membered N-benzoylamino-N-heterocycles. Analogous N-Boc-and N-carbamoyl hydrazides under microwave irradiation are intramolecularly aminocarbonylated to give bicyclic pyrazoles. -(ROVEDA, J.-G.; CLAVETTE, C.; HUNT, A. D.; GORELSKY, S. I.; WHIPP, C. J.; BEAUCHEMIN*, A. M.; J. Am. Chem. Soc. 131 (2009) 25, 8740-8741; Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.; Eng.) -Klein 48-040

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