Abstract
Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst due to photocleavage of the photolabile protecting group (PPG) and ensuing phenolate chelation to the ruthenium. The simple removal of the external filter after CM allows further photochemical reactions with UV-C light to achieve more complex architectures, such as the coumarins presented in this work. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 2352-2357 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 359 |
| Issue number | 14 |
| DOIs | |
| State | Published - 17 Jul 2017 |
Bibliographical note
Funding Information:The United States – Israel Binational Science Foundation (Grant No. 2014116) is gratefully acknowledged for partial funding of this research. The Open University is acknowledged for partial financial support.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- catalysis
- coumarins
- olefin metathesis
- photochemistry
- photolabile protecting groups
- ruthenium