A copper-catalyzed decarboxylative and oxidative decarbonylative cross-coupling of cinnamic acids with aliphatic aldehydes was achieved. The reaction undergoes subsequent decarbonylation, radical addition and decarboxylation processes with aliphatic aldehydes as the cheap and abundant alkyl radical source. This procedure offers a complementary approach to the convenient generation of alkyl-substituted E-alkenes.

The development of the palladium-catalyzed allylic alkylation of in situ generated boron enolates via tandem 1,4-hydroboration is reported. Investigation of the reaction revealed insights into specific catalyst electronic features as well as a profound leaving group effect that proved crucial for achieving efficient allylic alkylation of ester enolates at room temperature and ultimately a highly preparatively useful synthesis of notoriously challenging acyclic all-carbon quaternary stereocenters. The method demonstrates boron enolates as viable pro-nucleophiles in transition-metal catalyzed allylic alkylation, potentially opening up further transformations outside their traditional use.