6533b827fe1ef96bd12866a4

RESEARCH PRODUCT

9,10-Phenanthrenedione as Visible-Light Photoredox Catalyst: A Green Methodology for the Functionalization of 3,4-Dihydro-1,4-Benzoxazin-2- Ones through a Friedel-Crafts Reaction

Gonzalo BlayCarlos VilaJaume Rostoll-berenguerJosé R. Pedro

subject

010402 general chemistrylcsh:Chemical technology01 natural sciencesCatalysisCatalysislcsh:Chemistrychemistry.chemical_compoundCatàlisiTryptophollcsh:TP1-1185Lewis acids and basesorganic_chemistryPhysical and Theoretical ChemistryFriedel-Crafts reactionFriedel–Crafts reaction010405 organic chemistryindolesCombinatorial chemistry0104 chemical scienceschemistrylcsh:QD1-999visible-light photocatalysis14-benzoxazin-2-onesPhotocatalysisSurface modificationorganophotoredox catalysisQuímica orgànicaDerivative (chemistry)Visible spectrum

description

A visible-light photoredox functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones through a Friedel-Crafts reaction with indoles using an inexpensive organophotoredox catalyst is described. The reaction uses a dual catalytic system that is formed by a photocatalyst simple and cheap, 9,10-phenanthrenedione, and a Lewis acid, Zn(OTf)2. 5W white LEDs are used as visible-light source and oxygen from air as a terminal oxidant, obtaining the corresponding products with good yields. The reaction can be extended to other electron-rich arenes. Our methodology represents one of the most valuable and sustainable approach for the functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones, as compared to the reported procedures. Furthermore, several transformations were carried out, such as the synthesis of the natural product cephalandole A and a tryptophol derivative.

yearjournalcountryeditionlanguage
2018-12-12
10.3390/catal8120653http://hdl.handle.net/10550/68282