Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction

Nat Commun. 2022 Sep 26;13(1):5642. doi: 10.1038/s41467-022-33452-0.

ABSTRACT

The enantioselective pyridinylation is important for providing chiral compounds bearing heterocycles of pharmaceutical interests. 4-CN-pyrinde is extensively applied in the radical pyridinylation reaction, however, its’ enantioselective application is highly challenging. To achieve this goal, we propose an electrochemical catalytic activation of 4-CN-pyridine with a chiral transition metal complex instead of direct cathodic reduction. The chiral catalyst acts as the electron mediator and the transition metal catalysis in turn. The radical species from 4-CN-pyridine is captured via radical rebound by chiral catalyst, and undergoes enantioselective pyridinylation reaction. Here, we show the first method for catalytic asymmetric allylic 4-pyridinylation reactions using 4-CN-pyridine under electrochemical conditions.

PMID:36163325 | DOI:10.1038/s41467-022-33452-0

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