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Synlett 2017; 28(19): 2609-2613
DOI: 10.1055/s-0036-1590937
DOI: 10.1055/s-0036-1590937
cluster
Synthesis of Fluorine-Containing Tetraarylanthracenes via Ruthenium-Catalyzed C–O or C–F Arylation and their Crystal Structures
This work was supported in part by JSPS KAKENHI Grant Numbers JP15H05839 in Middle Molecular Strategy, and CREST and ACT-C (Grant Number JPMJCR12Y8) from the Japan Science and Technology Agency (JST), Japan. H.K. gratefully acknowledges the Japan Society for the Promotion of Science (JSPS) for a Research Fellowship for Young Scientists (JP16J02904). T.K. is also grateful for support by JSPS KAKENHI Grant Number 16H01040 (Precisely Designed Catalysts with Customized Scaffolding).Further Information
Publication History
Received: 02 August 2017
Accepted after revision: 26 September 2017
Publication Date:
08 November 2017 (online)
Published as part of the Cluster C–O Activation
Abstract
Tetraarylanthracenes containing several fluoro groups were synthesized using the ruthenium-catalyzed C–O or C–F arylation with arylboronates and their structural and spectroscopic studies were conducted. The RuH2(CO)(PPh3)3-catalyzed C–O arylation of aromatic ketones was found to be effective for the introduction of aryl groups containing multiple fluoro groups. Anthracenes possessing fluorinated aryl groups were prepared in two steps from 1,4,5,8-tetramethoxyanthraquinone by C–O arylation and reduction of the carbonyl groups. A tetraphenylanthracene containing a fluorinated anthracene moiety was also prepared using C–F phenylation of octafluoroanthraquinone. Single-crystal X-ray diffraction analysis showed that the positions of fluoro groups on the tetraarylanthracenes lead to notable difference in the crystal packing structures. The larger difference between the tetraarylanthracenes was observed in the fluorescence spectra in the solid state than those in chloroform.
Key words
C–O bond cleavage - C–F bond cleavage - ruthenium catalyst - tetraarylanthracenes - fluoroarenes - crystal structures - fluorescence spectra - arylboronatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590937.
- Supporting Information
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