Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization

Abstract

(Z)-Cinnamate derivatives are prevalent in natural bioactive products and in organic synthesis. Herein, we report a practical approach toward the efficient synthesis of (Z)-cinnamate derivatives via visible-light-driven isomerization. When E-isomers of cinnamate derivatives were irradiated with blue light in the presence of 1 mol% Ir₂(ppy)₄Cl₂ (ppy = 2-phenylpyridine), Z-isomers were readily obtained in good yields. This strategy allows the large-scale synthesis of (Z)-cinnamate derivatives with simple purification. This convenient, mild, and green synthetic methodology was subsequently applied to the synthesis of coumarins.

Key words

visible light - isomerization - Ir₂(ppy)₄Cl₂ - cinnamate - coumarins

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