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Abstract We report a new protocol for palladium‐catalyzed acetoxylation of the γ‐C( sp 3 )H bonds of N ‐alkylpicolinamide substrates using PhI(OAc) 2 oxidant. These reactions involve the use of substoichiometric amounts of Li 2 CO 3 additive, which effectively suppresses the competing intramolecular CH amination process. Under these conditions, N ‐propylpicolinamides bearing α substituents can be cleanly converted to γ‐acetoxylated amine products in excellent yield. This CH acetoxylation can also be used in concert with other Pd‐catalyzed picolinamide‐directed CH functionalization reactions for rapid scaffold diversification. magnified image
Li et al. (Wed,) studied this question.