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Abstract
<p class="first" id="P1">This Article describes the development of a second-generation
catalyst system for
the transannular C–H functionalization of alicyclic amines. Pyridine- and quinoline-carboxylate
ligands are shown to be highly effective for increasing the reaction rate, yield,
and scope of Pd-catalyzed transannular C–H arylation reactions of azabicyclo[3.1.0]hexane,
azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, and piperidine derivatives. Mechanistic
studies reveal that the pyridine/quinoline-carboxylates play a role in impeding both
reversible and irreversible catalyst decomposition pathways. These ligands enable
the first reported examples of the transannular C–H arylation of the ubiquitous tropane,
7-azanorbornane, and homotropane cores. Finally, the pyridine/quinoline-carboxylates
are shown to promote both transannular C–H arylation and transannular C–H dehydrogenation
on a homotropane substrate.
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