Metal catalyzed oxidative cross-couplings between two different nucleophilic components can offer advantages over alternative forms of contemporary coupling reactions, particularly with regard to tolerance towards reactive electrophilic functional groups. However, efficient coupling without undesirable substrate oxidation or homo-coupling presents a persistent difficulty. Inspired by the Chan-Lam reaction, our group has developed copper-mediated oxidative arylation processes using aryl boron reagents and weak CH acids capable of undergoing decarboxylation. This presentation will discuss key observations and experimental parameters that allowed for reaction development, mechanistic aspects of the process, and applications in bioactive molecule synthesis and functionalization.

Oxidative carbon-carbon bond forming processes inspired by the Chan-Lam reaction

2019 Fall National Meeting

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