助教・芝原 文利

経 歴

出生地:奈良県 昭和49年7月17日生

学 歴
平成5年4月 同志社大学工学部工業化学科 入学
平成9年3月 同志社大学工学部工業化学科 卒業
平成9年4月 京都大学大学院工学研究科材料化学専攻修士課程 入学
平成11年3月 京都大学大学院工学研究科材料化学専攻修士課程 修了
平成11年4月 京都大学大学院工学研究科材料化学専攻博士後期課程 進学
平成12年9月〜 京都大学大学院工学研究科材料化学専攻博士後期課程 休学 
平成14年12月 京都大学大学院工学研究科材料化学専攻博士後期課程 退学

職 歴
平成12年10月〜平成15年3月 JSTさきがけ21・野崎京子グループメンバー
(平成12年10月〜平成14年3月 京都大学工学部檜山研究室
 平成14年4月〜平成15年3月 東京大学工学部野崎研究室)
平成15年4月〜 岐阜大学工学部応用化学科村井研究室 助手
平成19年4月〜 岐阜大学工学部応用化学科村井研究室 助教(制度改変により) 現在に至る
平成25年4月〜 岐阜大学工学部応用化学科村井研究室 准教授 現在に至る

平成19年9月〜平成20年8月 University of Texas at Austin, Michael J. Krische Group,
Visiting Faculty as Donald D. Harrington Faculty Fellow

受 賞
平成18年度有機合成化学協会研究企画賞(武田薬品工業研究企画賞)受賞
平成19年9月 2008-2009 Donald D. Harrington Faculty Fellows Program
平成21年7月 有機合成化学教会東海支部奨励賞 受賞


学 位
平成15年3月 博士(工学)京都大学 (檜山爲次郎先生・野崎京子先生の御指導)
題目:Studies on Asymmetric Carbonylation by Means of Polystyrene-Supported Transition Metal Catalysts

専門分野:有機合成化学、不斉合成、遷移金属触媒化学

e-mail : fshiba:gifu-u.ac.jp (:を@に換えてお使いください)

研究業績

論文

32. Diastereo- and Regioselective Addition of Thioamide Dianions to Imines and Aziridines: Syntheses of N-Thioacyl 1,2-, and 1,3-Diamines
Shibahara, F.; Kobayashi, S.; Maruyama, T.; Murai, T. Chem. −Eur. J. 2013, 19, 304-313.
http://dx.doi.org/10.1002/chem.201203470

31. One-pot Sequential Direct C-H Bond Arylation of Azoles Catalyzed by [Pd(phen)2](PF6)2
Shibahara, F.; Yamauchi, T.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2012, 77, 8815-8820.
http://dx.doi.org/10.1021/jo301621t

30. Palladium-catalyzed C-H bond direct alkynylation of 5-membered heteroarenes: A well-defined synthetic route to azole derivatives containing two different alkynyl groups
Shibahara, F.; Dohke, Y.; Murai, T. J. Org. Chem. 2012, 77, 5381-5388.
http://dx.doi.org/10.1021/jo3008385

29. Imidazo[1,5-a]pyridine-1-ylalkylalcohols: synthesis via intramolecular cyclization of N-thioacyl 1,2-aminoalcohols and their silyl ethers and molecular structures
Murai, T.; Nagaya, E.; Shibahara, F.; Maruyama, T. Org. Biomol. Chem. 2012, 10, 4943-4953.
http://dx.doi.org/10.1039/C2OB25438G

28. 1-Alkynyl- and 1-Alkenyl-3-arylimidazo[1,5-a]pyridines: Synthesis, Photophysical Properties, and Observation of a Linear Correlation Between the Fluorescent Wavelength and Hammett Substituent Constants
Yamaguchi, E.; Shibahara, F.; Murai, T. J. Org. Chem. 2011, 76, 6146-6158.
http://dx.doi.org/10.1021/jo200864x

27. Direct Sequential C3 and C1 Arylation Reaction of Imidazo[1,5-a]pyridine Catalyzed by a 1,10-Phenanthroline Palladium Complex
Yamaguchi, E.; Shibahara, F.; Murai, T. Chem. Lett. 2011, 40, 939-940.
http://dx.doi.org/10.1246/cl.2011.939

26. Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation
Shibahara, F.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2011, 76, 2680-2693.
http://dx.doi.org/10.1021/jo200067y

25. Sequential one-pot reactions of thioformates with lithium silylacetylides, arylmagnesium halides, and electrophiles leading to formation of propargyl sulfides
Murai, T.; Ohashi, T.; Shibahara, F. Chem. Lett. 2011, 40, 70-71.
http://dx.doi.org/10.1246/cl.2011.70

24. (Selenocarbamoyl)silanes and -germanes: Their Synthesis Using (Selenocarbamoyl)lithium and Characterization
Murai, T.; Hori, R.; Maruyama, T.; Shibahara, F. Organometallics 2010, 29, 2400-2402.
http://dx.doi.org/10.1021/om100290h

23. Direct multiple C-H bond arylation reaction of heteroarenes catalyzed by cationic palladium complex bearing 1,10-phenanthroline
Shibahara, F.; Yamaguchi, E.; Murai, T. Chem. Commun. 2010, 46, 2471-2473.
http://dx.doi.org/10.1039/b920794e

22."Direct Thionation and Selenation of Carbonyl Compounds Using Elemental Sulfur and Selenium with Hydrochlorosilanes in the Presence of Amines”
Shibahara, F.; Sugiura, R.; Murai, T. Org. Lett. 2009,11, 3064-3067.
http://dx.doi.org/10.1021/ol9010882

21."Synthesis of Fluorescent 1,3-Diarylated Imidazo[1,5-a]pyridines: Oxidative Condensation−Cyclization of Aryl-2-Pyridylmethylamines and Aldehydes Using Elemental Sulfur as an Oxidant"
Shiibahara, F.; Sugiura, R.; Kitagawa, A.; Yamaguchi, E.; Murai, T. J. Org. Chem. 2009, 74, 3566-3568.
http://dx.doi.org/10.1021/jo900415y

20."Synthesis of 1,3-Diarylated Imidazo[1,5-a]pyridines with a Combinatorial Approach: Metal-catalyzed Cross-coupling Reactions of 1-Halo-3-aryl-imidazo[1,5-a]pyridines with Arylmetal Reagents"
Shiibahara, F.; Yamaguchi, E.; Kitagawa, A.; Imai, A.; Murai, T. Tetrahedron 2009, 65, 5062-5073.
http://dx.doi.org/10.1016/j.tet.2009.02.062

19."Diene Hydroacylation from the Alcohol or Aldehyde Oxidation Level via Ruthenium-Catalyzed C-C Bond-Forming Transfer Hydrogenation: Synthesis of β,γ-Unsaturated Ketones"
Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120−14122.
http://dx.doi.org/10.1021/ja805356j

18."Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents"
Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338-6339.
http://dx.doi.org/10.1021/ja801213x
Highlighted in C&E News 2008, 86(19), 10: http://pubs.acs.org/cen/news/86/i19/8619notw4.html
Highlighted in Synfact 2008, 8, 0831: http://dx.doi.org/10.1055/s-2008.1077906

17."Copper-catalyzed Oxidative Desulfurization-promoted Intramolecular Cyclization of Thioamides Using Molecular Oxygen as an Oxidant: An Efficient Route to Five- to Seven-membered Nitrogen-containing Heterocycles"
Shibahara, F.; Yoshida, A.; Murai, T. Chem. Lett. 2008, 37, 646-647.
http://dx.doi.org/10.1246/cl.2008.646

16."Synthesis of 1,1'-Binaphthyl-2,2'-diyl Phosphoroselenoic Ammonium Salts and their Conversion to Optically Active Dialkyl Diselenides"
Murai. T.; Monzaki, M.; Shibahara, F. Chem. Lett. 2007, 36, 852-853.
http://dx.doi.org/10.1246/cl.2007.852

15."Copper-catalyzed oxidative desulfurization−oxygenation of thiocarbonyl compounds using molecular oxygen: an efficient method for the preparation of oxygen isotopically labeled carbonyl compounds"
Shibahara, F.
; Suenami, A.; Yoshida, A.; Murai, T. Chem. Commun. 2007, 2354-2356.
http://dx.doi.org/10.1039/b701048f

14."Synthesis of 1,1'-Binaphthyl-2,2'-diyl Phosphoroselenoic Amides and Their Conversion to Optically Pure Phosphoramidites"
Murai, T.; Inaji, S.; Morishita, K. Shibahara, F.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Chem. Lett. 2006, 35, 1424-1425.
http://dx.doi.org/10.1246/cl.2006.1424

13."Synthesis of 2-Azaindolizines by Using an Iodine-Mediated Oxidative Desulfurization Promoted Cyclization of N-2-pyridylmethyl Thioamides and an Investigation of Their Photophysical Propaerties"
Shibahara, F.; Kitagawa. A.; Yamaguchi, E.; Murai, T. Org. Lett. 2006, 24, 5621-5624.
http://dx.doi.org/10.1021/ol0623623

12."N-Thioacyl 1,3-Amino Alcohols: Synthesis via Ring-Opening of Oxiranes with Thioamide Dianions and Applications as Key Intermediates Leading to Stereochemically Defined 5,6-Dihydro-4H-1,3-oxazines and 1,3-Amino Alcohols"
Murai, T.; Sano, H.; Kawai, H.; Aso, H.; Shibahara, F. J. Org. Chem. 2005, 70, 8148-8153.
http://dx.doi.org/10.1021/jo051378o

11."Comparison of two preparative methods: a polymer-supported catalyst by metal-complexation with a polymeric ligand or by polymerization of a metal complex"
Kinoshita, S.; Shibahara, F.; Nozaki, K. Green Chem. 2005, 7, 256-258.
http://dx.doi.org/10.1039/b418264b

10."Palladium(II)-Catalyzed Sequential Hydroxylation-Carboxylation of Biphenyl Using Formic Acid as a Carbonyl Source"
Shibahara. F.; Kinoshita, S.; Nozaki, K. Org. Lett. 2004, 6, 2437-2439.
http://dx.doi.org/10.1021/ol049166l

9."Iodo-cyclization of N-Homoallyl Thioamides Leading to 2,4-Diaryl-5,6-dihydro-4H-1,3-thiazines"
Murai, T.; Niwa, H.; Kimura, T.; Shibahara, F.
Chem. Lett.
2004, 33, 508-509.
http://dx.doi.org/10.1246/cl.2004.508

8."Solvent-Free Asymmetric Olefin Hydroformylation Catalyzed by Highly Crosslinked Polystyrene-Supported (R,S)-BINAPHOS-Rh(I) Complex"
Shibahara, F.
; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 8555-8560.
http://dx.doi.org/10.1021/ja034447u

7."High Pressure IR Studies on the Asymmetric Hydroformylation of Styrene Catalyzed by Rh(I)–(R,S)-BINAPHOS'es"
Nozaki, K.; Matsuo, T.; Shibahara, F.; Hiyama, T. Organometallics 2003, 22, 594-600.
http://dx.doi.org/10.1021/om020245f

6."Asymmetric Hydroformylation with Highly Crosslinked Polystyrene-supported (R,S)-BINAPHOS–Rh(I) Complexes: the Effect of Immobilization Position"
Shibahara, F.
; Nozaki, K.; Matsuo, T.; Hiyama, T. Bioorg. Med. Chem. Lett. 2002, 12, 1825-1827.
http://dx.doi.org/10.1016/S0960-894X(02)00267-6

5."Alternating Copolymerization of w-Perfluoroalkyl-1-alkenes with Carbon Monoxide Catalyzed by Homogeneous and Polymer-supported Pd-complexes"
Nozaki, K.; Shibahara, F.; Elzner, S.; Hiyama, T. Can. J. Chem. 2001, 79, 593-597.
http://dx.doi.org/10.1139/cjc-79-5-6-593

4."Substituent Effect in Asymmetric Hydroformylation of Olefins Catalyzed by Rhodium(I) Complexes of (R,S)-BINAPHOS Derivatives: A Protocol for Improvement of Regio- and Enantioselectivities" Nozaki, K.; Matsuo, T.; Shibahara, F.; Hiyama, T. Adv. Synth. Catal. 2001, 343, 61-63.
http://dx.doi.org/10.1002/1615-4169(20010129)343:1<61::AID-ADSC61>3.0.CO;2-L

3."Vapor-phase Asymmetric Hydroformylation"
Nozaki, K; Shibahara, F.; Hiyama, T. Chem. Lett. 2000, 694-695.
http://dx.doi.org/10.1246/cl.2000.694

2."Asymmetric Hydroformylation of Olefins in Highly Cross-Linked Polymer Matrixes"
Nozaki, K; Shibahara, F.; Itoi, Y.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. Bull. Chem. Soc. Jpn. 1999, 72, 1911-1918.
http://dx.doi.org/10.1246/bcsj.72.1911

1."Asymmetric Hydroformylation of Olefins in a Highly Cross-Linked Polymer Matrix"
Nozaki, K.; Itoi, Y.; Shibahara, F.; Shirakawa, E.; Ohta, T.; Takaya, H.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 4051-4052.
http://dx.doi.org/10.1021/ja973408d

総説など

5. Development of organic reactions by means of oxidative or reductive activation of sulfur atom
硫黄原子の酸化的・還元的活性化を経る有機合成反応の開発
Shibahara, F.; Murai, T. 有機合成化学協会誌 2011, 69, 28-37.
http://dx.doi.org/10.5059/yukigoseikyokaishi.69.28

4. "有機EL材料探索―含窒素縮環10π-電子系”アザインドリジン類”の電子材料への展開―"
芝原文利; 村井利昭 月刊ディスプレイ (Written in Japanese)

3. "Formation of C-C Bonds via Ruthenium Catalyzed Transfer Hydrogenation: Carbonyl Addition from the Alcohol or Aldehyde Oxidation Level"
Shibahara, F.
; Krische, M. J. Chem. Lett. 2008, 1102-1107.
http://dx.doi.org/10.1246/cl.2008.1102

2. "Efficient Synthetic Method for Novel Azaindolizines as Organic Light-Emitting Devices”
“新規なアザインドリジン系有機EL用化合物の効率的な合成法”
Murai, T.; Shibahara, F. 化学工業, 2008, 59, 686-691. (Written in Japanese)

1."高架橋ポリスチレン担持(R,S)-BINAPHOS–Rh(I)錯体を用いる不斉ヒドロホルミル化反応"
芝原文利
; 野崎京子; 檜山爲次郎. 有機合成化学協会誌 2003, 61, 694-705.(Written in Japanese)

特許

4. "DNA損傷チェックポイント活性化剤"
木村賢一、土屋英子、芝原文利、村井利昭
特許公開2008-105963

3. "2−アザインドリジン類の製造方法、2−アザインドリジン類金属錯体の製造方法及び2−アザインドリジン類金属錯体"
芝原文利、村井利昭
WO2006/088028

2. "カルボニル化合物の製造方法"
芝原文利、村井利昭、末次藍子
特許2006-056827

1. "アレーン類とギ酸とからワンポットで前記アレーン類をカルボキシル化および/またはヒドロキシル化した化合物を製造する方法"
玉尾京子、芝原文利
WO2004/076397

趣味:音楽鑑賞、料理、機械いじり

(updated in Apr. 3. 2013)