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

Abstract

The Pd(II)-catalyzed sp³ 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.

Key words

palladium - C–H bond activation - benzoxylation - aldehydes - α-amino acid derivatives

Publication History

Received: 17 January 2021

Accepted after revision: 10 March 2021

Accepted Manuscript online:
10 March 2021

Article published online:
19 April 2021

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