Readily Removable Directing Group Assisted Chemo- and Regioselective C(sp(3))-H Activation by Palladium Catalysis.

Currently used directing groups for selective aliphatic β-functionalization of carbonyl compounds show excellent reactivity and selectivity with an amide as a linker. Described herein is 2-piconimide, used for the first time with commercially available 2-picolinamide/2-picolic acid as precursors, to direct C-H arylation/alkenylation by palladium catalysis. The directing group is essential for promoting the sequnetial primary and secondary C(sp(3))-H arylation with different aryl iodides in one substrate. The directing group was easily removed under simple reaction conditions at room temperature.