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Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single‐Electron‐Transfer Oxidizing Process

2010; Wiley; Volume: 122; Issue: 19 Linguagem: Inglês

10.1002/ange.200907281

1521-3757

Toshifumi Dohi, Motoki Ito, Nobutaka Yamaoka, Koji Morimoto, Hiromichi Fujioka, Yasuyuki Kita,

Catalytic C–H Functionalization Methods

Angewandte ChemieVolume 122, Issue 19 p. 3406-3409 Zuschrift Unusual ipso Substitution of Diaryliodonium Bromides Initiated by a Single-Electron-Transfer Oxidizing Process† Toshifumi Dohi Dr., Toshifumi Dohi Dr. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829 Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorMotoki Ito, Motoki Ito Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorNobutaka Yamaoka, Nobutaka Yamaoka College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this authorKoji Morimoto Dr., Koji Morimoto Dr. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this authorHiromichi Fujioka Prof. Dr., Hiromichi Fujioka Prof. Dr. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorYasuyuki Kita Prof. Dr., Yasuyuki Kita Prof. Dr. kita@ph.ritsumei.ac.jp College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this author Toshifumi Dohi Dr., Toshifumi Dohi Dr. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829 Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorMotoki Ito, Motoki Ito Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorNobutaka Yamaoka, Nobutaka Yamaoka College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this authorKoji Morimoto Dr., Koji Morimoto Dr. College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this authorHiromichi Fujioka Prof. Dr., Hiromichi Fujioka Prof. Dr. Graduate School of Pharmaceutical Sciences, Osaka University, 1–6 Yamada-oka, Suita, Osaka 565-0871 (Japan)Search for more papers by this authorYasuyuki Kita Prof. Dr., Yasuyuki Kita Prof. Dr. kita@ph.ritsumei.ac.jp College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829Search for more papers by this author First published: 20 April 2010 https://doi.org/10.1002/ange.200907281Citations: 66 † This work was supported by Grants-in-Aid for Scientific Research (A) from the Japan Society for the Promotion of Science (JSPS), Grants-in-Aid for Young Scientists (B) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), and the Ritsumeikan Global Innovation Research Organization (R-GIRO) project. T.D. acknowledges support from the Industrial Technology Research Grant Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan. M.I. acknowledges a Research Fellowship for Young Scientists from JSPS. Read the full textAboutPDF ToolsRequest permissionAdd to favorites ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Iod kuppelt: Die Umsetzung der Diaryliodoniumbromide 1 mit aromatischen Nucleophilen 2 ergab eine Reihe von Heterobiarylen 3 in guten Ausbeuten. Diese ipso-Substitution am Heteroarenring von 1 verläuft über aromatische Radikalkationen, die durch Einelektronentransfer(SET)-Oxidation von 2 erzeugt werden. HFIP=Hexafluor-2-propanol. Citing Literature 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. Filename Description ange_200907281_sm_miscellaneous_information.pdf85.3 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume122, Issue19April 26, 2010Pages 3406-3409 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. 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