J-GLOBAL         Last updated: Jul 2, 2019 at 02:42
Gifu University
Faculty of Engineering
Ph. D.(Kyoto University)

Research Areas


Academic & Professional Experience

Researcher, PRESTO, JST, Nozaki Group


Apr 1993
Mar 1997
Department of Industrial Chemistry, Department of Engineering, Doshisha University
Apr 1997
Mar 1999
Material Chemistry, School of Engineering, Kyoto University
Apr 1999
Dec 2003
Material Chemistry, School of Engineering, Kyoto University

Awards & Honors

Dec 2014

Published Papers

Fumitoshi Shibahara, Yusuke Asai, Toshiaki Murai
Asian Journal of Organic Chemistry   7(7) 1323   Jul 2018   [Refereed]
Fumitoshi Shibahara, Yusuke Asai, Toshiaki Murai
Asian Journal of Organic Chemistry   7(7) 1134   Jul 2018   [Refereed]
Fumitoshi Shibahara, Masafumi Suzuki, Saki Kubota, Tomoki Fukunaga, Taro Udagawa, Toshiaki Murai
The Journal of Organic Chemistry      Mar 2018   [Refereed]
Koto Y, Shibahara F, Murai T
Organic & biomolecular chemistry   15(8) 1810-1820   Feb 2017   [Refereed]
Yuma Koto, Fumitoshi Shibahara, Toshiaki Murai
Chemistry Letters   45 1327-1329   Jan 2016
© 2016 The Chemical Society of Japan.The transfer hydrogenation of carbonyl compounds catalyzed by Rh and Ir complexes bearing 1-substituted-imidazo[1,5-a]pyridin-3-ylidene ligands is reported. These catalysts, especially the Rh catalyst, showed h...
Takayuki Yamauchi, Fumitoshi Shibahara, Toshiaki Murai, Toshiaki Murai
Organic Letters   17 5392-5395   Nov 2015   [Refereed]
? 2015 American Chemical Society. A direct C-H bond arylation method for thienyl thioamides catalyzed by [Pd(phen)2](PF6)2 was developed. This reaction selectively afforded 2-monoarylated products, while the corresponding amide thiophene derivativ...
Toshiaki Murai, Toshiaki Murai, Eri Nagaya, Fumitoshi Shibahara, Toshifumi Maruyama, Hiroshi Nakazawa
Journal of Organometallic Chemistry   794 76-80   Jul 2015   [Refereed]
? 2015 Elsevier B.V. Abstract Rh(I) and Ir(I) complexes bearing imidazo[1,5-a]pyridine-1-ylalkyl alcohol as chelating N?†O-monoanionic ligands were prepared as thermally stable compounds. Their spectroscopic properties and structures were determin...
Yamauchi Takayuki, Shibahara Fumitoshi, Murai Toshiaki
The Journal of organic chemistry   79(15) 7185-7192   Aug 2014   [Refereed]
C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen)2](PF6)2, has been developed. The process tolerates the presence of a variety of functional groups on ...
Shibahara Fumitoshi, Kanai Takafumi, Yamaguchi Eiji, Kamei Akika, Yamauchi Takayuki, Murai Toshiaki
Chemistry, an Asian journal   9(1) 237-244   Jan 2014   [Refereed]
The reactions of aromaticcompounds and elemental chalcogens catalyzed by a copper salt with molecular oxygen as an oxidant were carried out. The reaction of 3-substituted imidazo[1,5-a]pyridines and elemental sulfur in the presence of CuTC (copper...
Toshiaki Murai, Toshiaki Murai, Eri Nagaya, Keitaro Miyahara, Fumitoshi Shibahara, Toshifumi Maruyama
Chemistry Letters   42 828-830   Aug 2013   [Refereed]
Imidazo[1,5-a]pyridin-1-ylalkyl alcohols were reacted with diphenylborinic acid to give boron complexes in which nitrogen and oxygen atoms were coordinated to a boron atom. The use of imidazo[1,5-a]pyridin-1-ylalkyl alcohol with two 2-pyridyl grou...
Fumitoshi Shibahara, Toshiaki Murai
Asian Journal of Organic Chemistry   2 624-636   Jan 2013   [Refereed][Invited]
Significant progress has been made in transition-metal-catalyzed direct functionalization of heteroarenes since the beginning of the 21st century. Particularly, palladium-catalyzed direct C-H arylations of heteroarenes have been extensively studie...
Shibahara Fumitoshi, Kobayashi Shun-ichiro, Maruyama Toshifumi, Murai Toshiaki
Chemistry (Weinheim an der Bergstrasse, Germany)   19(1) 304-313   Jan 2013   [Refereed]
Addition reactions of thioamide dianions that were derived from N-arylmethyl thioamides to imines and aziridines were carried out. The reactions of imines gave the addition products of N-thioacyl-1,2-diamines in a highly diastereoselective manner ...
Shibahara Fumitoshi, Yamauchi Takayuki, Yamaguchi Eiji, Murai Toshiaki
The Journal of organic chemistry   77(19) 8815-8820   Oct 2012   [Refereed]
Synthetic methods for triarylated azoles containing threedifferent aryl groups via one-pot sequential multiple C-H bond arylations are described. The one-pot sequential diarylation of C5-monoarylated azoles was achieved by the simple sequential ad...
Murai Toshiaki, Nagaya Eri, Shibahara Fumitoshi, Maruyama Toshifumi
Organic&biomolecular chemistry   10(25) 4943-4953   Jul 2012   [Refereed]
Iodine-mediated cyclization of N-thioacyl 1,2-aminoalcohols derived from aromatic aldehydes and ketones mainly produced bis(1-imidazo[1,5-a]pyridyl)arylmethanes, whereas the reaction of N-thioacyl 1,2-aminoalcohols derivedfrom aliphatic aldehydes ...
Shibahara Fumitoshi, Dohke Yoshimasa, Murai Toshiaki
The Journal of organic chemistry   77(12) 5381-5388   Jun 2012   [Refereed]
A widely applicable oxidative coupling of 5-membered heteroarenes and terminal alkynes that uses a combination of palladium and silver salts was developed. Under suitable conditions, imidazole and benzimidazole, which are sluggish under similar pr...
Fumitoshi Shibahara, Toshiaki Murai
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   69(1) 28-37   Dec 2011   [Refereed]
Organosulfur compounds play an important role in organic synthesis owing to their unique reactivities. We have been focusing on development of transformation and synthesis of organosulfur compounds. In this account, we describe our recent advances...
Eiji Yamaguchi, Fumitoshi Shibahara, Toshiaki Murai
Chemistry Letters   40(9) 939-940   Sep 2011   [Refereed]
The direct sequential arylation reaction at the C3 and C1 positions of imidazo[1,5-a]pyridines with a variety of aryl iodides catalyzed by [Pd(phen) 2](PF 6) 2 is described. The reaction of unsubstituted imidazo[1,5-a]pyridine with various aryl io...
Eiji Yamaguchi, Fumitoshi Shibahara, Toshiaki Murai
Journal of Organic Chemistry   76(15) 6146-6158   Aug 2011   [Refereed]
1-Alkynyl- and 1-alkenyl-3-arylimidazo[1,5-a]pyridines were synthesized. The Sonogashira coupling of 3-aryl-1-iodoimidazo[1,5-a]pyridines and various terminal alkynes with Pd(PPh 3) 2Cl 2 (10 mol %) and CuI (10 mol %) in triethylamine at 80 °C for...
Fumitoshi Shibahara, Eiji Yamaguchi, Toshiaki Murai
Journal of Organic Chemistry   76(8) 2680-2693   Apr 2011   [Refereed]
Direct triarylation and sequential triarylation reactions of simple azoles catalyzed by [Pd(phen) 2]PF 6 are described. Simple azoles, such as N-methylimidazole, thiazole, and oxazole, were observed to undergo triaryaltion reactions even at their ...
Toshiaki Murai, Takayuki Ohashi, Fumitoshi Shibahara
Chemistry Letters   40(1) 70-71   Jan 2011   [Refereed]
One-pot reactions of thioformates with lithium silylacetylides, arylmagnesium halides, and electrophiles that produce propargyl (2-propynyl) sulfides are described. The pathway for this process begins with addition of lithium (trimethylsilyl)acety...
Toshiaki Murai, Rumi Hori, Toshifumi Maruyama, Fumitoshi Shibahara
Organometallics   29 2400-2402   Jun 2010   [Refereed]
Deprotonation of the selenoformyl group in N,N-dibenzyl selenoformamide with LDA, followed by silylation and germylation of the resulting anion with Me3SiCl and Me3GeCl, gives (selenocarbamoyl)silane and -germane in moderate to good yields. The mo...
Fumitoshi Shibahara, Eiji Yamaguchi, Toshiaki Murai
Chemical Communications   46 2471-2473   Mar 2010   [Refereed]
A cationic palladium complex bearing 1,10-phenanthroline ligand is found to catalyze direct C-H arylation reactions of heteroarenes with aryl iodides to give mono-, di-, or tri-arylated products selectively. ? The Royal Society of Chemistry.
Shinsuke Tahara, Fumitoshi Shibahara, Toshifumi Maruyama, Toshiaki Murai
Chemical Communications   7009-7011   Dec 2009   [Refereed]
The treatment of N-thioacyl-1-(2-pyridyl)-1,2-aminoalcohols with iodine and pyridine in THF at room temperature for 30 min leads to the formation of bis(1-imidazo[1,5-a]pyridyl)arylmethanes as green solids in good to high yields. ? The Royal Socie...
15(9) 32-38   Sep 2009
Fumitoshi Shibahara, Rie Sugiura, Toshiaki Murai
Organic Letters   11 3064-3067   Jul 2009   [Refereed]
Reactions of amides with elemental sulfur in the presence of hydrochlorosilanes and amines give the corresponding thioamides in good to high yields. The process takes place via reduction of elemental sulfur by the hydrochlorosilane in the presence...
Fumitoshi Shibahara, Eiji Yamaguchi, Asumi Kitagawa, Akio Imai, Toshiaki Murai
Tetrahedron   65 5062-5073   Jun 2009   [Refereed]
The halogenation of 3-arylimidazo[1,5-a]pyridines was carried out with iodine, bromine, N-chlorosuccinimide, and 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate as halogenating agents to give selectively halogenated products 1-halo-3-arylimid...
Fumitoshi Shibahara, Rie Sugiura, Eiji Yamaguchi, Asumi Kitagawa, Toshiaki Murai
Journal of Organic Chemistry   74 3566-3568   May 2009   [Refereed]
Oxidative condensation - cyclization of aldehydes and aryl-2- pyridylmethylamines proceeded in the presence of a stoichiometric amount of elemental sulfur as an oxidant in the absence of catalyst. The reaction gave a variety of 1,3-diarylated imid...
Fumitoshi Shibahara, Michael J. Krische
Chemistry Letters   37 1102-1107   Dec 2008   [Refereed]
Under the conditions of ruthenium-catalyzed transfer hydrogenation employing isopropyl alcohol as terminal reductant, π-un-saturated compounds (1,3-dienes, allenes, 1,3-enynes, and al-kynes) reductively couple to aldehydes to furnish products of c...
Fumitoshi Shibahara, John F. Bower, Michael J. Krische
Journal of the American Chemical Society   130 14120-14122   Oct 2008   [Refereed]
Under the conditions of ruthenium-catalyzed transfer hydrogenation, isoprene couples to benzylic and aliphatic alcohols 1a-g to deliver β,γ-unsaturated ketones 3a-g in good to excellent isolated yields. Under identical conditions, aldehydes 2a-g c...
59 686-691   Sep 2008
Fumitoshi Shibahara, Atsunori Yoshida, Toshiaki Murai
Chemistry Letters   37 646-647   Jun 2008   [Refereed]
Copper-catalyzed oxidative desulfurization-promoted intramolecular cyclization reactions of thioamides take place under neutral and mild conditions by using molecular oxygen as an oxidant. The process yields a wide variety of nitrogen-containing h...
Fumitoshi Shibahara, John F. Bower, Michael J. Krische
Journal of the American Chemical Society   130 6338-6339   May 2008   [Refereed]
Under the conditions of ruthenium-catalyzed transfer hydrogenation, commercially available acyclic 1,3-dienes, butadiene, isoprene, and 2,3-dimethylbutadiene, couple to benzylic alcohols 1a-6a to furnish products of carbonyl crotylation 1b-6b, car...
Toshiaki Murai, Masaki Monzaki, Fumitoshi Shibahara
Chemistry Letters   36 852-853   Jul 2007   [Refereed]
Optically pure phosphoroselenoyl chloride reacted with Et 3N in the presence of H 2O to give a phosphoroselenoic tertiary ammonium salt. Formation of the salt was confirmed by X-ray molecular structure analysis. The quaternary ammonium salt was pr...
Fumitoshi Shibahara, Aiko Suenami, Atsunori Yoshida, Toshiaki Murai
Chemical Communications   2354-2356   Jun 2007   [Refereed]
A novel copper-catalyzed oxidative desulfurization reaction of thiocarbonyl compounds, using molecular oxygen as an oxidant and leading to formation of carbonyl compounds, has been developed, and the utility of the process is demonstrated by its a...
Toshiaki Murai, Shinsuke Inaji, Ken Morishita, Fumitoshi Shibahara, Makoto Tokunaga, Yasushi Obora, Yasushi Tsuji
Chemistry Letters   35 1424-1425   Dec 2006   [Refereed]
Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatograp...
Fumitoshi Shibahara, Asumi Kitagawa, Eiji Yamaguchi, Toshiaki Murai
Organic Letters   8(24) 5621-5624   Nov 2006   [Refereed]
Iodine-mediated, oxidative desulfurization promoted cyclization of N-2-pyridylmethyl thioamides serves as an efficient and versatile method for the preparation of 2-azaindolizines (imidazo[1,5-a]pyridines) and rare 2-azaindolizine sulfur-bridged d...
Toshiaki Murai, Hiroaki Sano, Hiroyasu Kawai, Hideo Aso, Fumitoshi Shibahara
Journal of Organic Chemistry   70 8148-8153   Sep 2005   [Refereed]
N-Thioacyl 1,3-amino alcohols were synthesized via the ring-opening of oxiranes with thioamide dianions generated from N-benzyl thioamides and BuLi in a highly regio- and stereoselective manner. The diastereomers of N-thioacyl 1,3-amino alcohols w...
Shinsuke Kinoshita, Fumitoshi Shibahara, Fumitoshi Shibahara, Kyoko Nozaki, Kyoko Nozaki
Green Chemistry   7(5) 256-258   May 2005   [Refereed]
The difference between two methods for the synthesis of polystyrene-supported (R,S)-BINAPHOS-Rh(I) complex, namely (1) copolymerization of the monomeric ligand with divinylbenzene-ethylstyrene and then Rh-complex formation with the polymer-support...
Fumitoshi Shibahara, Fumitoshi Shibahara, Shinsuke Kinoshita, Kyoko Nozaki, Kyoko Nozaki
Organic Letters   6 2437-2439   Jul 2004   [Refereed]
(Equation Presented) A simultaneous hydroxylation-carboxylation of biphenyl occurred to give 4′-hydroxy-4-biphenylcarboxylic acid, which has wide potential application as a polyester monomer.
Toshiaki Murai, Hisayuki Niwa, Tsutomu Kimura, Fumitoshi Shibahara
Chemistry Letters   33 508-509   May 2004   [Refereed]
Iodo-cyclization of N-homoallyl thioamides was carried out in the presence of Et3N to form 2,4-diaryl-5,6-dihydro-4H-1,3-thiazines in good to high yields. The reaction of thioamides bearing 1-naphthyl or 2-methoxyphenyl group at the carbon atom ad...
Fumitoshi Shibahara, Fumitoshi Shibahara, Kyoko Nozaki, Kyoko Nozaki, Tamejiro Hiyama
Journal of the American Chemical Society   125(28) 8555-8560   Jul 2003   [Refereed]
Using an (R,S)-BINAPHOS-Rh(I) catalyst that is covalently anchored to a highly cross-linked polystyrene support, asymmetric hydroformylation of olefins was performed in the absence of organic solvents. The reaction of cis-2-butene, a gaseous subst...
Fumitoshi Shibahara, Kyoko Nozaki, Tamejiro Hiyama
J. Syn. Org. Chem. Jpn.   61 694-705   Jul 2003   [Refereed]
Using highly cross-linked polystyrene-supported chiral phosphine-phosphite (R, S)-BINAPHOS-Rh(I) complexes, olefins were hydroformylated to give the corresponding iso-aldehydes in high ee's in benzene suspension. The efficiency in catalytic activi...
Kyoko Nozaki, Kyoko Nozaki, Takeshi Matsuo, Fumitoshi Shibahara, Tamejiro Hiyama
Organometallics   22 594-600   Feb 2003   [Refereed]
Rhodium-catalyzed asymmetric hydroformylation of styrene using (R,S)-BINAPHOS (1a) and its methoxy-substituted derivative 1b as chiral ligands was monitored by in situ high-pressure IR. The rate of aldehyde production is given by robs = kobs[Rh]1....
Fumitoshi Shibahara, Kyoko Nozaki, Kyoko Nozaki, Takeshi Matsuo, Tamejiro Hiyama
Bioorganic and Medicinal Chemistry Letters   12 1825-1827   Jul 2002   [Refereed]
A new class of polymer-supported (R,S)-BINAPHOS 1e in which the parent BINAPHOS has two alkoxy-substituents at the 3-positions of the phenyls, has been synthesised. Using its Rh(I) complex, asymmetric hydroformylation of olefins proceeded with hig...
K. Nozaki, F. Shibahara, S. Elzner, T. Hiyama
Canadian Journal of Chemistry   79 593-597   Aug 2001   [Refereed]
Alternating copolymerization of fluorinated olefins (CnF2n + 1)(CH2)mCH=CH2 (1) and carbon monoxide was carried out using cationic Pd(II)-(R,S)-BINAPHOS complexes (2) as catalysts. To obtain polymeric products sufficiently, existence of at least t...
Kyoko Nozaki, Takeshi Matsuo, Fumitoshi Shibahara, Tamejiro Hiyama
Advanced Synthesis and Catalysis   343 61-63   Jan 2001   [Refereed]
Kyoko Nozaki, Fumitoshi Shibahara, Tamejiro Hiyama
Chemistry Letters   694 694-695   Dec 2000   [Refereed]
Polystyrene-supported (R,S)-BINAPHOS-Rh complex was demonstrated to be applicable to the asymmetric hydroformylation of gaseous substrates in a non-solvent system: 3,3,3-trifluoropropene (2a) and (Z)-2-butene (2b) were converted into the correspon...
Kyoko Nozaki, Fumitoshi Shibahara, Yohei Itoi, Eiji Shirakawa, Tetsuo Ohta, Tetsuo Ohta, Hidemasa Takaya, Tamejiro Hiyama
Bulletin of the Chemical Society of Japan   72 1911-1918   Aug 1999   [Refereed]
When polymer-immobilized chiral phosphine-phosphite-Rh(I) complexes were used, the asymmetric hydroformylation of styrene gave 2- and 3- phenylpropanals with a substrate/catalyst ratio of 2000, iso/normal ratios of 84/16 to 89/11, and 89% R enanti...


Toshiaki Murai, Akihito Yoshida, Tomohiko Mizutani, Hiroaki Kubuki, Kirara Yamaguchi, Toshifumi Maruyama, Fumitoshi Shibahara
Chemistry Letters   46 1017-1019   Jan 2017
© 2017 The Chemical Society of Japan. The reactions of 2-pyrones and coumarins with hydrochlorosilane, elemental selenium, and 4-dimethylaminopyridine (DMAP) gave 2-selenopyrones and selenocoumarins in moderate to good yields. Their formation was ...
Takayuki Yamauchi, Fumitoshi Shibahara, Toshiaki Murai
Tetrahedron Letters   57 2945-2948   Jan 2016
© 2016 Elsevier Ltd. All rights reserved. The arylative cyclization of o-(1-alkynyl)thioanisoles with aryl iodides in the presence of catalytic amounts of [Pd(phen)2][PF6]2resulted in the efficient formation of 3-arylated benzo[b]thiophenes, and a...

Association Memberships


Research Grants & Projects

Catalytic Transformation of Sulfur Containing Compounds
Project Year: 2003   
Ministry of Education, Culture, Sports, Science and Technology: Grants-in-Aid for Scientific Research
Project Year: 2013 - 2014
Japan Society for the Promotion of Science: Grants-in-Aid for Scientific Research
Project Year: 2013 - 2014