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      Synthesis of Dibenzofurans from Cyclic Diaryliodonium Triflates and Water via Oxygen–Iodine Exchange Approach

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          Abstract

          An efficient synthesis of a variety of dibenzofuran derivatives via Cu-catalyzed cyclization diaryliodonium salts in water is achieved. Various dibenzofuran derivatives could be obtained in good to excellent yields via this oxygen–iodine exchange approach. A concise synthesis of organic semiconducting material molecule has been achieved using this method.

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          Synthesis of ladder-type pi-conjugated heteroacenes via palladium-catalyzed double N-arylation and intramolecular O-arylation.

           Koji Nakano,  Keiko Kawaguchi,  Kyoko Nozaki (2007)
          Ladder-type heteroacenes containing pyrrole or furan rings, indolo[3,2-b]carbazoles and dibenzo[d,d']benzo[1,2-b:4,5-b']difurans, were effectively synthesized from the common intermediates, 2,5-bis(o-chloroaryl)hydroquinones. The key reactions are palladium-catalyzed double N-arylation of aniline and intramolecular O-arylation, which enable regioselective ring closure. In addition to the parent indolo[3,2-b]carbazole and dibenzo[d,d']benzo[1,2-b:4,5-b']difuran, their derivatives with an alkyl or cyano group were first synthesized. Photophysical and electrochemical studies showed that the obtained heteroacenes have lower HOMO energy levels and larger band gaps than the corresponding hydrocarbon acene, pentacene. An X-ray analysis of dibenzo[d,d']benzo[1,2-b:4,5-b']difuran revealed that it was packed in herringbone fashion.
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            Synthesis of Carbazoles and Dibenzofurans via Cross-Coupling ofo-Iodoanilines ando-Iodophenols with Silylaryl Triflates

             Richard C. Larock,  Zhijian Liu (2004)
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              Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

               Stefan Riedmüller,  Boris J Nachtsheim (2013)
              Summary The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues.
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 10 October 2018
                Publication date Collection: 31 October 2018
                Volume: 3
                Issue: 10
                Pages: 12923-12929
                Affiliations
                †School of Pharmaceutical Engineering & Life Sciences and ‡School of Petrochemical Engineering, Changzhou University , Changzhou 213164, China
                Author notes
                Article
                DOI: 10.1021/acsomega.8b02345
                PMC ID: 6644658
                Copyright statement: Copyright © 2018 American Chemical Society
                License:

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

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                Subject: Article
                Custom metadata
                document-id-old-9 ao8b02345
                document-id-new-14 ao-2018-02345t
                ccc-price

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