B/Pd Synergistic Catalysis for the Decarboxylative Allylation of 2-(2-Azaaryl)acetic Acids.

Abstract

We describe an allylation reaction between 2-(2-azaaryl)acetic acids and allylic electrophiles catalyzed synergistically by a dual system consisting of borinic acid and a Pd complex under mild conditions. The decarboxylative allylation proceeds via a boron-bound enamine intermediate, which then interacts with a π-allylpalladium intermediate from the allylic electrophile. High yields of diallylation products highlight the method's efficiency. Intriguingly, when using 2-(2-pyridyl)acetic acid with a C3 substituent on the pyridyl ring, the reaction exclusively yields monoallylation products.