Full Paper
Synthesis of a Library of Fluorescent 2-Aryl-3-trifluoromethylnaphthofurans from Naphthols by Using a Sequential Pummerer-Annulation/Cross-Coupling Strategy and their Photophysical Properties
Yuuya Ookubo,
Prof. Dr. Atsushi Wakamiya,
Prof. Dr. Hideki Yorimitsu,
Prof. Dr. Atsuhiro Osuka,
Yuuya Ookubo
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Search for more papers by this authorProf. Dr. Atsushi Wakamiya
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Search for more papers by this authorYuuya Ookubo,
Prof. Dr. Atsushi Wakamiya,
Prof. Dr. Hideki Yorimitsu,
Prof. Dr. Atsuhiro Osuka,
Yuuya Ookubo
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Search for more papers by this authorProf. Dr. Atsushi Wakamiya
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502 (Japan), Fax: (+)81-75-753-3970
Search for more papers by this authorGraphical Abstract
Generation next: Pummerer annulation of simple naphthols followed by cross-coupling with various arylzinc reagents allows the concise and diversity-oriented synthesis of a library of fluorescent naphthofurans (see scheme).
Abstract
A library of 2-aryl-3-trifluoromethylnaphthofurans was synthesized with high efficiency from simple naphthols. In this synthesis, the Pummerer-type annulation of naphthols with 3-(2,2,2-trifluoroethylidene)-2,4-dithiapentane 2-oxide was followed by a cross-coupling of the resulting 2-methylthio-3-trifluoromethylnaphthofurans with a variety of arylzinc reagents. A palladium complex, Pd-PEPPSI-IPr, was the most efficient catalyst for the arylation step, which represents the first cross-coupling of aryl sulfides by using an N-heterocyclic-carbene-ligated palladium complex. This library consists of new π-expanded molecules, all of which are fluorescent in the solid state as well as in solution. Their photophysical properties, such as absorption and emission, fluorescence quantum yields, and fluorescence lifetimes, were thoroughly investigated. This library was also useful to identify acidochromic molecules.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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