研究者詳細 - 岡内　辰夫

論文 - 岡内　辰夫

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Pd-catalyzed cyclization of terminal alkynes using diazonaphthoquinones: Synthesis of naphtho[1,2-b]furans 査読有り国際誌

Takahashi S., Shimooka H., Okauchi T., Kitamura M.

Chemistry Letters 48 ( 1 ) 28 - 31 2019年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2019 The Chemical Society of Japan. Naphtho[1,2-b]furans were synthesized via a Pd-catalyzed reaction of diazonaphthoquinones and terminal alkynes in the presence of CuI and diisopropylamine. This method was then successfully applied to the synthesis of natural product, furomollugin.

DOI： 10.1246/cl.180803

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85059438494&origin=inward

高校生のためのクロスカップリング実験:—ノーベル化学賞の鈴木-宮浦クロスカップリングを題材に— 査読有り

岡内辰夫, 北村充

化学と教育 ( 公益社団法人日本化学会 ) 67 ( 3 ) 130 - 133 2019年01月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

<p>2010年，「有機合成におけるパラジウム触媒を用いたクロスカップリングの開発」に貢献した3人（Heck，根岸，鈴木）に，ノーベル化学賞が与えられた。そのうち2人が日本人であったため，マスコミで大きく取り上げられ，クロスカップリングという言葉が広く知られるようになった。受賞者の1人である北海道大学名誉教授の鈴木　章先生らのグループが開発した反応が，鈴木-宮浦クロスカップリングである。この反応は，有機ホウ素化合物と有機ハロゲン化合物に対して，パラジウム触媒を作用させることで炭素-炭素結合が形成するというものである。この反応は，我々の身の回りの医薬品，農薬，液晶材料，EL材料などの開発・量産化に大いに貢献している。</p>

DOI： 10.20665/kakyoshi.67.3_130

CiNii Article

その他リンク： https://ci.nii.ac.jp/naid/130007804205

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone 査読有り国際誌

Othman D., Otsuka K., Takahashi S., Selim K., El-Sayed M., Tantawy A., Okauchi T., Kitamura M.

Synlett 29 ( 4 ) 457 - 462 2018年03月

記述言語：英語掲載種別：研究論文（学術雑誌）

© Georg Thieme Verlag Stuttgart New York. The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs-Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag 2 O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

DOI： 10.1055/s-0036-1589118

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85033366665&origin=inward

Synthesis of 1,2-naphthalenediol derivatives by Rh-catalyzed intermolecular O[sbnd]H insertion reaction of 1,2-diazonaphthoquinones with water and alcohols 査読有り国際誌

Kitamura M., Otsuka K., Takahashi S., Okauchi T.

Tetrahedron Letters 58 ( 36 ) 3508 - 3511 2017年09月

担当区分：最終著者記述言語：英語掲載種別：研究論文（学術雑誌）

DOI： 10.1016/j.tetlet.2017.07.084

Scopus

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Synthesis of (±)-myo-inositol 4-methylenephosphonate via Rh-Catalyzed hydrogenation of vinylphosphonate 査読有り国際誌

Tatsuo Okauchi, Shuya Nakamura, Kouta Tsubaki, Momoko Asakawa, Mitsuru Kitamura

Carbohydrate Research 448 24 - 27 2017年08月

担当区分：筆頭著者,　責任著者記述言語：英語掲載種別：研究論文（学術雑誌）

Phosphatidylinositol phosphate (PIP) synthetase is a promising target for the development of new anti-mycobacterium compounds. We previously reported that myo-inositol 1-methylenephosphonate showed inhibitory activity against PIP synthetase. Herein, we report the synthesis of unprotected myo-inositol 4-methylenephosphonate, a constitutional isomer of myo-inositol 1-methylenephosphonate and found that the stereoselective hydrogenation of vinylphosphonate proceeded via Rh catalysis.

DOI： 10.1016/j.carres.2017.05.018

Scopus

その他リンク： http://www.sciencedirect.com/science/article/pii/S0008621517303269

Synthesis, characterization and air stable semiconductor properties of thiophene-condensed pyrene derivatives 査読有り

Moriguchi T., Higashi M., Yakeya D., Jalli V., Tsuge A., Okauchi T., Nagamatsu S., Takashima W.

Journal of Molecular Structure 1127 413 - 418 2017年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Elsevier B.V.New and simple polyaromatic compounds containing two thiophene rings were prepared via photo-cyclization and their structural and photophysical properties were evaluated via 1H NMR spectroscopy and X-ray crystallographic analysis. On the basis of X-ray analysis, it was determined that the molecular structure of the compound was highly strained and that they contain two hetero [4] helicene moieties. The compounds were investigated as active layer in p-type organic field-effect transistors (p-OFET) in top contact type devices. Notably, the compound containing two thiophene components exhibited very stable p-type semiconducting behavior in moist air.

DOI： 10.1016/j.molstruc.2016.07.104

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84982811017&origin=inward

Molecular structures of n-type semiconducting material 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} and its photo dimerization product 査読有り

Moriguchi T., Kitou N., Jalli V., Yoza K., Nagamatsu S., Okauchi T., Tsuge A., Takashima W.

Journal of Molecular Structure 1118 372 - 377 2016年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Elsevier B.V. All rights reserved.The absolute molecular structure of air stable n-type semiconducting material 2,5-difluoro-1,4-phenylene-3,3′-bis{2-[(4-trifluoromethyl)phenyl]acrylonitrile} was determined by using twin crystal treatment X-ray diffraction analysis. The compound was readily dimerized in solution via irradiating of UV or Sun light. The exact molecular structure of the dimer also determined by X-ray analysis.

DOI： 10.1016/j.molstruc.2016.04.035

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84964329369&origin=inward

Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl 査読有り

Kitamura M., Fukuma H., Kobayashi M., Okayama S., Okauchi T.

Journal of Organic Chemistry 81 ( 9 ) 3956 - 3960 2016年05月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 American Chemical Society.Bifunctional C2-symmetric 7,7′-dihydroxymethyl-8,8′-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7′-dimethyl-8,8′-biquinolyl (3) is stable. Optically active 2 was obtained through separation of racemic 2 by chiral column HPLC or Pd(II)-catalyzed double C-H oxidation of optically active 3. The absolute stereochemistry of enantiomers of 2 and 3 was determined using the exciton chirality method.

DOI： 10.1021/acs.joc.6b00534

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84968735850&origin=inward

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate 査読有り

Kitamura M., Ishikawa A., Okauchi T.

Tetrahedron Letters 57 ( 16 ) 1794 - 1797 2016年04月

記述言語：英語掲載種別：研究論文（学術雑誌）

© 2016 Published by Elsevier Ltd.Two chiral 2-azidoimidazolinium salts [(7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate (2) and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate (3)] were synthesized, and their structures were determined by X-ray single crystal structural analysis. Migratory amidation reaction of enol silyl ether with 3 proceeded, but good diastereoselectivity was not observed in the reaction.

DOI： 10.1016/j.tetlet.2016.03.036

Scopus

その他リンク： https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84962261604&origin=inward

Pinpoint-fluorinated phenanthrene synthesis based on C-F bond activation of difluoroalkenes 査読有り

K. Fuchibe, T. Morikawa, R. Ueda, T. Okauchi, J. Ichikawa

Journal of Fluorine Chemistry 179 106 - 115 2015年11月

Rh-Catalyzed Cyclization of 3-Aryloxycarbonyldiazonaphthoquinones for the Synthesis of beta-Phenylnaphthalene Lactones and Formal Synthesis of Pradimicinone 査読有り

M. Kitamura, S. Takahashi, T. Okauchi

The Journal of Organic Chemistry 80 ( 16 ) 8406 - 8416 2015年08月

Thermodynamics and kinetic studies in the binding interaction of cyclic naphthalene diimide derivatives with double stranded DNAs 査読有り

M. M. Islam, S. Fujii, S. Sato, T. Okauchi, S. Takenaka

Bioorganic & Medicinal Chemistry 23 ( 15 ) 4769 - 4776 2015年08月

Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction 査読有り

M. Kitamura, R. Sakata, N. Tashiro, A. Ikegami, T. Okauchi

Bulletin of the Chemical Society of Japan 88 ( 6 ) 824 - 833 2015年06月

A Selective G-Quadruplex DNA-Stabilizing Ligand Based on a Cyclic Naphthalene Diimide Derivative 査読有り

M. M. Islam, S. Fujii, S. Sato, T. Okauchi, S. Takenaka

Molecules 20 ( 6 ) 10963 - 10979 2015年06月

Unprecedented formation of hapto4-(vinylketene)iron complexes from hapto4-(diene)iron complexes and aromatic compounds in the presence of a Lewis acid 査読有り

Tatsuo Okauchi, Naoki Sata, Akihiro Urakawa, Mitsuru Kitamura

Chemical Communications 51 ( 40 ) 8454 - 8456 2015年05月

Long-Term Air-Stable n-Channel Organic Thin-Film Transistors Using 2,5-Difluoro-1,4-phenylene-bis{2-[4-(trifluoromethyl)phenyl]acrylonitrile} 査読有り

Shuichi Nagamatsu, Shinya Oku, Kouji Kuramoto, Tetsuji Moriguchi, Wataru Takashima, Tatsuo Okauchi, Shuzi Hayase

ACS Applied Materials & Interfaces 6 3847 - 3852 2014年03月

Pd(OAc)2-Catalyzed Macrocyclization of 1,2-Diazonaphthoquinones with Cyclic Ethers 査読有り

Mitsuru Kitamura, Masato Kisanuki, Koichi Kanemura, Tatsuo Okauchi

Organic Letters 16 ( 6 ) 1554 - 1557 2014年03月

A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate 査読有り

Mitsuru Kitamura, So Kato, Masakazu Yano, Norifumi Tashiro, Yuichiro Shiratake, Mitsuyoshi Sandoa, Tatsuo Okauchi

Organic & Biomolecular Chemistry 12 ( 25 ) 4397 - 4406 2014年01月

Rhodium-Catalyzed Reaction of Diazonaphthoquinones and Enol Ethers: Synthesis of Dihydronaphthofuran Derivatives and alpha-Naphthyl Esters 査読有り

Mitsuru Kitamura, Keiichiro Araki, Hiroki Matsuzaki, Tatsuo Okauchi

European Journal of Organic Chemistry 2013 ( 23 ) 5045 - 5049 2013年08月

Synthesis of alpha-Arylcarboxylic Acid Amides from Silyl Enol Ether via Migratory Amidation with 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate 査読有り

Mitsuru Kitamura, Kento Murakami, Yuichiro Shiratake, Tatsuo Okauchi

Chemistry Letters 42 ( 7 ) 691 - 693 2013年07月

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