Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis

Autor:	Ofer Reany, Revannath L. Sutar, N. Gabriel Lemcoff, Or Eivgi
Rok vydání:	2017
Předmět:	010405 organic chemistry Chemistry UV filter chemistry.chemical_element General Chemistry 010402 general chemistry Photochemistry Photosynthesis 01 natural sciences 0104 chemical sciences Ruthenium Catalysis Filter (video) Chelation Irradiation Protecting group
Zdroj:	Advanced Synthesis & Catalysis. 359:2352-2357
ISSN:	1615-4150
DOI:	10.1002/adsc.201700316
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e2786dd16bcdd2745a0989aa528a243d https://doi.org/10.1002/adsc.201700316 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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