CC BY-ND-NC 4.0 · SynOpen 2019; 03(04): 103-107
DOI: 10.1055/s-0039-1690331
letter
Copyright with the author(s) (2019) The author(s)

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

Penghua Shu
,
Haichang Xu
,
Lingxiang Zhang
,
Junping Li
,
Hao Liu
,
Yuehui Luo
,
Xue Yang
,
Zhiyu Ju
,
Zhihong Xu
This work was financially supported by the National Natural Science Foundation of China (No. 21702178), the Key Scientific Research Project of Colleges and Universities in Henan Province (No. 18A350010), the Science and Technology Department of Henan Province (No. 182102311108), and the Excellent Young Key Teacher Funding Project of Xuchang University (No. 2017).
Further Information

Publication History

Received: 22 August 2019

Accepted after revision: 12 September 2019

Publication Date:
09 October 2019 (online)

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.

Supporting Information

 
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