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Visible-Light-Driven, Photocatalyst-Free Cascade to Access 3-Cyanoalkyl Coumarins from ortho -Hydroxycinnamic Esters.

Authors :
Hu YZ
Ye ZP
Xia PJ
Song D
Li XJ
Liu ZL
Liu F
Chen K
Xiang HY
Yang H
Source :
The Journal of organic chemistry [J Org Chem] 2021 Mar 05; Vol. 86 (5), pp. 4245-4253. Date of Electronic Publication: 2021 Feb 19.
Publication Year :
2021

Abstract

A visible-light-driven, photocatalyst-free route starting from easily accessed ortho -hydroxycinnamic esters and O -perfluoropyridin-4-yl oximes has been successfully developed to rapidly assemble a wide range of 3-cyanoalkyl coumarins. This process does not require addition of external photocatalysts, exhibiting beneficial features including mild reaction conditions, synthetic simplicity, and excellent substrate compatibility. Extensive mechanistic investigations revealed that the in situ generated phenolate anions served as photosensitizers to drive this photoinduced transformation.

Details

Language :
English
ISSN :
1520-6904
Volume :
86
Issue :
5
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
33606932
Full Text :
https://doi.org/10.1021/acs.joc.1c00024