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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 6
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Original Articles

An Improved Procedure for Diazotization Fluoro-Dediazoniation of Anilines Using Organic Base-HF Agents

Tsuyoshi Fukuhara Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, 060
,
Norihiko Yoneda Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, 060
,
Teiken Sawada Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, 060
&
Akira Suzuki Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo, 060
Pages 685-692 | Published online: 19 Dec 2006

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Kojchi Shinhama, Shinji Aki, Takuya Furuta & Jun-ichi Minamikawa. (1993) Facile Conversion of Arenediazonium Salts to the Corresponding Fluoroarenes Using Boron Trifluoride Diethyl Ether Complex. Synthetic Communications 23:11, pages 1577-1582.
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Norihiko Yoneda, Tsuyoshi Fukuhara, Tetsuo Kikuchi & Akira Suzuki. (1989) Preparation of Aromatic Fluorides Via Diazotization and Photochemically Induced Fluoro-Dediazoniation of Aromatic Amines in Anhydrous Hydrogen Fluoride - Organic Base Solutions. Synthetic Communications 19:5-6, pages 865-871.
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Articles from other publishers (30)

Takashi Okazoe & Yuichiro Ishibashi. 2023. Industrial Arene Chemistry. Industrial Arene Chemistry 1723 1767 .
Kevin Simon, Desiree Znidar, Julien Boutet, Gérard Guillamot, Jean-Yves Lenoir, Doris Dallinger & C. Oliver Kappe. (2023) Generation of 1,2-Difluorobenzene via a Photochemical Fluorodediazoniation Step in a Continuous Flow Mode. Organic Process Research & Development 27:2, pages 322-330.
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Jiming Liu, Duoheng Wang, Qilin Xu, Hangwei Yu, Jiadi Zhou, Zhiqun Yu & Weike Su. (2020) Continuous-flow double diazotization for the synthesis of m-difluorobenzene via Balz-Schiemann reaction. Journal of Flow Chemistry 10:4, pages 589-596.
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Chuanfa Ni, Bo Xing & Jinbo Hu. 2020. Fluorination. Fluorination 31 36 .
Chuanfa Ni, Bo Xing & Jinbo Hu. 2020. Fluorination. Fluorination 1 6 .
Carolina Torres-García, Daniel Pulido, Fernando Albericio, Miriam Royo & Ernesto Nicolás. (2014) Triazene as a Powerful Tool for Solid-Phase Derivatization of Phenylalanine Containing Peptides: Zygosporamide Analogues as a Proof of Concept. The Journal of Organic Chemistry 79:23, pages 11409-11415.
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. (2010) Synthesis of Some Biologically Active Halogenopurines. Journal of the Korean Chemical Society 54:4, pages 429-436.
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Heinrich Zollinger. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
Shlomo Rozen. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
. (2005) Aromatic Fluorination by Decomposition of Triazenes in Ionic Liquids. Bulletin of the Korean Chemical Society 26:4, pages 599-602.
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Hui-Yin Li. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Max M. Boudakian. 2000. Kirk‐Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology.
Norihiko Yoneda. (2000) Progress in the preparation of organo-fluorine compounds using HF or HF–base molten salts. Journal of Fluorine Chemistry 105:2, pages 205-207.
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Tamejiro HiyamaTamejiro Hiyama & Hisashi Yamamoto. 2000. Organofluorine Compounds. Organofluorine Compounds 25 76 .
Charles L. Cywin, Janice M. Klunder, MaryAnn Hoermann, Janice R. Brickwood, Eva David, Peter M. Grob, Racheline Schwartz, Daniel Pauletti, Kevin J. Barringer, Cheng-Kon Shih, Christopher L. Sorge, David A. Erickson, David P. Joseph & Susan E. Hattox. (1998) Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 8. 8-Aryloxymethyl- and 8-Arylthiomethyldipyridodiazepinones. Journal of Medicinal Chemistry 41:16, pages 2972-2984.
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Masanori Tamura, Motonari Shibakami & Akira Sekiya. (1998) Deaminative Fluorination of Anilines with Silicon Tetrafluoride: Utility of Silicon Tetrafluoride as a Fluorine Source. European Journal of Organic Chemistry 1998:4, pages 725-727.
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Patricia A. Pieper, Ding-yah Yang, Hui-qiang Zhou & Hung-wen Liu. (1997) 3-Deoxy-3-fluoropyridoxamine 5‘-Phosphate:  Synthesis and Chemical and Biological Properties of a Coenzyme B 6 Analog . Journal of the American Chemical Society 119:8, pages 1809-1817.
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Masanori Tamura, Motonari Shibakami, Shigeru Kurosawa, Takashi Arimura & Akira Sekiya. (1996) Deaminative fluorination of anilines using potassium hydrogen fluoride and silicon tetrafluoride. Journal of Fluorine Chemistry 78:1, pages 95-96.
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Norihiko Yoneda & Tsuyoshi Fukuhara. (1996) Facile preparation of aromatic fluorides by deaminative fluorination of aminoarenes using hydrogen fluoride combined with bases. Tetrahedron 52:1, pages 23-36.
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Koshi Sasaki, Mari Oishi & Naoshi Imaki. (1996) An improved method for fluoro-dediazoniation of arylamines substituted with polar groups. Journal of Fluorine Chemistry 76:1, pages 59-62.
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. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1103 1295 .
Christopher J. Urch. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 605 633 .
Tsuyoshi Fukuhara, Manabu Sekiguchi & Norihiko Yoneda. (1994) Facile Preparation of Aromatic Fluorides by the Fluoro-Dediazoniation of Aromatic Diazonium Tetrafluoroborates Using HF-Pyridine Solution. Chemistry Letters 23:6, pages 1011-1012.
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Norihiko Yoneda. (1991) The combination of hydrogen fluoride with organic bases as fluorination agents. Tetrahedron 47:29, pages 5329-5365.
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Tsuyoshi Fukuhara, Satoshi Sasaki, Norihiko Yoneda & Akira Suzuki. (1990) Preparation of Fluoroarenes in One-Pot Diazotization and Fluoro-Dediazoniation of Aminoarenes Using HF or HF-Base. The Functions of Bases in the HF Solution. Bulletin of the Chemical Society of Japan 63:7, pages 2058-2062.
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Yasuo Yoshida & Yoshikazu Kimura. (1989) An improved and practical synthesis of 4-fluorobenzaldehyde by halogen-exchange fluorination reaction. Journal of Fluorine Chemistry 44:2, pages 291-298.
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G. K. Surya Prakash & George A. Olah. (1988) Synthetic methods and reactions. Proceedings / Indian Academy of Sciences 100:2-3, pages 143-185.
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Tsuyoshi Fukuhara, Norihiko Yoneda & Akira Suzuki. (1988) A facile preparation of fluoropyridines from Aminopyridines via diazotization and fluorodediazoniation in HF or HF-pyridine solutions. Journal of Fluorine Chemistry 38:3, pages 435-438.
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T. FUKUHARA, N. YONEDA, T. SAWADA & A. SUZUKI. (2016) ChemInform Abstract: An Improved Procedure for Diazotization‐Fluorodediazoniation of Anilines Using Organic Base ‐ HF Agents.. ChemInform 19:4.
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. 1988. Annual Reports in Organic Synthesis–1987. Annual Reports in Organic Synthesis–1987 376 426 .

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