In this study, we systematically evaluate different ambiphilic organohalides for their ability to participate in anti-selective carbo- or heteroannulation with non-conjugated alkenyl amides under Pd /Pd catalysis. Detailed optimization of the reaction conditions has led to protocols for synthesizing tetrahydropyridines, tetralins, pyrrolidines, and other carbo/heterocyclic cores via [n+2] (n=3-5) (hetero)annulation. Expansion of scope to otherwise unreactive ambiphilic haloketones through Pd /amine co-catalysis is also demonstrated. Compared to other annulation processes, this method proceeds via a distinct Pd /Pd mechanism involving Wacker-type directed nucleopalladation. This difference results in unique reactivity and selectivity patterns, as revealed through assessment of reaction scope and competition experiments.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8923970 | PMC |
| http://dx.doi.org/10.1002/anie.202114346 | DOI Listing |
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