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

Kyalo Stephen Kanyiva; King Hung Nigel Tang; Jiarui Wang; Takanori Shibata

doi:10.1055/a-1422-9632

Synthesis, Table of Contents

Synthesis 2021; 53(17): 3085-3093
DOI: 10.1055/a-1422-9632

special topic

Bond Activation – in Honor of Prof. Shinji Murai

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

Kyalo Stephen Kanyiva∗

^aGlobal Center of Science and Engineering, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan

,

King Hung Nigel Tang

^bDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan

,

Jiarui Wang

^bDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan

,

Takanori Shibata ∗

^bDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan

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Abstract

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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

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References

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Supplementary Material

Supporting Information