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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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          Most cited references 17

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

          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

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              Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

              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
                ACS Omega
                ACS Omega
                ao
                acsodf
                ACS Omega
                American Chemical Society
                2470-1343
                10 October 2018
                31 October 2018
                : 3
                : 10
                : 12923-12929
                Affiliations
                School of Pharmaceutical Engineering & Life Sciences and School of Petrochemical Engineering, Changzhou University , Changzhou 213164, China
                Author notes
                Article
                10.1021/acsomega.8b02345
                6644658
                Copyright © 2018 American Chemical Society

                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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                ao8b02345
                ao-2018-02345t

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