Fluorescent diarylindoles by palladium-catalyzed direct and decarboxylative arylations of carboxyindoles.
Simple and brilliant: 1-Substituted 1H-indole-2-carboxylic acids efficiently undergo successive diarylation accompanied by C-H bond cleavage and decarboxylation upon treatment with aryl bromides in the presence of a palladium catalyst system to afford fluorescent 2,3-diarylindoles. This facile synthetic method provides a highly efficient blue emitter with a quantum yield of 0.97 in the solid state (see scheme).
Miyasaka
Mitsuru
M
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Fukushima
Azusa
A
Satoh
Tetsuya
T
Hirano
Koji
K
Miura
Masahiro
M
D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D005456:Fluorescent Dyes / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D014961:X-Ray Diffraction
D002264:Carboxylic Acids; D005456:Fluorescent Dyes; D007211:Indoles; D010165:Palladium; C030374:indole