Tokyo Institute of Technology · Pharmacology, Toxicology and Pharmaceutics
Professor Toshio Fuchigami's research lab specializes in sustainable and selective fluorination methodologies, with a focus on electrochemical and ionic liquid-based approaches for the synthesis of organofluorine compounds. The lab pioneers innovative techniques such as electrolytic partial fluorination and indirect anodic gem-difluorination, utilizing recyclable mediators and hypervalent iodine fluorides to achieve high regioselectivity. A key emphasis is placed on green chemistry principles, including the use of fluoride-containing ionic liquids and environmentally benign reaction media to minimize waste and enhance atom economy. The lab also explores the functionalization of polymers and heterocycles, demonstrating the versatility of fluorination in materials science and pharmaceutical applications.
Figures are computed from collected data and may differ slightly.
Organofluorine compounds are key materials applied in daily life because of their versatile utility as functional materials, pharmaceuticals, and agrochemicals. Development of the selective fluorination of organic molecules under safe conditions is therefore one of the most important subjects in modern synthetic organofluorine chemistry. Thus, various electrophilic fluorination reagents such as XeF<sub>2</sub>, (PhSO<sub>2</sub>)<sub>2</sub>NF (NFSI), Et<sub>2</sub>NSF<sub>3</sub> (DAST), (MeOCH
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrolytic Partial Fluorination of Organic Compounds. 14. The First Electrosynthesis of Hypervalent Iodobenzene Difluoride Derivatives and Its Application to Indirect Anodic gem-DifluorinationToshio Fuchigami and Toshiyasu FujitaCite this: J. Org. Chem. 1994, 59, 24, 7190–7192Publication Date (Print):December 1, 1994Publication History Published online1 May 2002Published inissue 1 December 1994https://pubs.acs.org/doi/10.1021/jo00103a003https://doi.o
This article provides an outline of recent studies on selective electrochemical fluorination in ionic liquid fluoride salts toward green sustainable chemistry. First, a brief historical background of electrochemical fluorination in organic solvents is provided, and some particular problems and unique solvent effects associated with this technique are briefly mentioned. Second, recent progress in selective fluorination and fluorodesulfurization of organic molecules and macromolecules in ionic liq
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrolytic partial fluorination of organic compounds. 1. Regioselective anodic monofluorination of organosulfur compoundsToshio Fuchigami, Moriyasu Shimojo, Akinori Konno, and Kiyono NakagawaCite this: J. Org. Chem. 1990, 55, 25, 6074–6075Publication Date (Print):December 1, 1990Publication History Published online1 May 2002Published inissue 1 December 1990https://pubs.acs.org/doi/10.1021/jo00312a006https://doi.org/10.1021/jo00312a006research-article
On the double: When a poly(3-methylthiophene) (PT) film is doped on a bipolar electrode with Bu4NPF6 as supporting electrolyte, the film includes PF6− anions with a composition gradient along the potential gradient on the electrode. The use of Et4NCl results in partial chlorination of the PT film that reflects the potential gradient of the bipolar electrode (see picture; inset: photograph of the film). Detailed facts of importance to specialist readers are published as ”Supporting Information”.
Prins cyclization of homoallylic alcohols, thiols, and amines with various aldehydes in an ionic liquid HF salt (Et(4)NF.5HF) afforded the corresponding 4-fluorinated heterocycles in excellent yields.
Charged up: The selective electrochemical fluorination of organic compounds using the alkali-metal fluoride KF under very mild reaction conditions has been accomplished (see scheme). The long-standing problems of low solubility of metal fluorides in organic solvent and low nucleophilicity of fluoride ions for fluorination have been overcome by the use of of poly(ethylene glycol). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur AtomToshio Fuchigami, Moriyasu Shimojo, and Akinori KonnoCite this: J. Org. Chem. 1995, 60, 11, 3459–3464Publication Date (Print):June 1, 1995Publication History Published online1 May 2002Published inissue 1 June 1995https://pubs.acs.org/doi/10.1021/jo00116a037https://d
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrolytic Partial Fluorination of Organic Compounds. 12. Selective Anodic Monofluorination of Fluoroalkyl and Alkyl SulfidesToshio Fuchigami, Akinori Konno, Kiyono Nakagawa, and Moriyasu ShimojoCite this: J. Org. Chem. 1994, 59, 20, 5937–5941Publication Date (Print):October 1, 1994Publication History Published online1 May 2002Published inissue 1 October 1994https://doi.org/10.1021/jo00099a023RIGHTS & PERMISSIONSArticle Views465Altmetric-Citations66L
Cathodic hydroxylation of organoboron compounds was successfully performed under an oxygen atmosphere, producing the corresponding phenol derivatives with high selectivity and efficiency.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrolytic partial fluorination of organic compounds. 4. Regioselective anodic monofluorination of 4-thiazolidinones and its application to the synthesis of monofluoro .beta.-lactamsToshio Fuchigami, Satoru Narizuka, and Akinori KonnoCite this: J. Org. Chem. 1992, 57, 14, 3755–3757Publication Date (Print):July 1, 1992Publication History Published online1 May 2002Published inissue 1 July 1992https://doi.org/10.1021/jo00040a003RIGHTS & PERMISSIONSArtic
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