Palladium-Catalyzed sp3 C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

The Pd(II)-catalyzed sp(3) C-H bond benzoxylation of N-phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert-butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.

Automated summary

The study describes the Pd(II)-catalyzed sp(3) C-H bond benzoxylation of N-phthaloylalanine derivatives using an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions. A benzoxylated product was obtained with up to 68% yield when reacting an alanine derivative and an aldehyde in a toluene/water co-solvent in the presence of palladium catalyst and tert-butyl hydroperoxide at room temperature. The protecting group of the resulting benzoxylated product was efficiently removed to produce a free amide in high yield.