Reversing the Reactivity of Palladium Hydrides Using Blue LED’s: Difunctionalization of Conjugated π-Systems

Key words

palladium catalysis - blue LED - palladium hydrides

Significance

The hydropalladation (monofunctionalization) of conjugated dienes and enynes is limited by the amount of molecular complexity that can be installed in a single step. Gevorgyan and Zhang report an effective difuntionalization of conjugated π-systems using blue LEDs to enhance the hydricity of the intermediate palladium hydride species, ultimately merging Pd⁰/Pd^II and Pd^I/Pd^II ­reactivities.

Comment

The authors performed deuterium labelling experiments, using deuterated diphenylsilane. Although the addition of silane was beneficial to the yield of the transformation, no deuterium ­incorporation was observed when employing Ph₂SiD₂. This result suggests that the Brønsted acid may act as the predominant hydrogen source for Pd–H.

Publication History

Article published online:
08 December 2023