I TOP I ACCESS I
〒606-8585 京都市左京区松ケ崎御所海道町
京都工芸繊維大学 大学院工芸科学研究科
生命物質科学域 物質合成化学専攻
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2021年


今野 勉, ニチアス時報, 2021, (3), 1–6 (https://www.nichias.co.jp/research/technique/period.html)

フッ素化合物は,医農薬品,ディスプレイ材料,高分子材料,化学エネルギー材料,半導体関連材料など,これまでさまざまな分野で活用されており,いまなお,その利用領域は拡大している。本稿では,化学反応の視点から,フッ素あるいはフッ素含有置換基の特性を解説することに主眼を置く。

2020年

19. Recent Adcances in Halogen Bond-Assisted Organic Synthesis


Shigeyuki Yamada, Tsutomu Konno*, Current Organic Chemistry, Bentham Science, 2020, 24(18), 2118–2152 (DOI: 10.2174/1385272823666191209112543)

Halogen bond interactions, which take place between an electrophilic halogen and the electron-pair of a Lewis base and exhibit high directionality (approximately 180°), are non-covalent bond interactions similar to the hydrogen bond interaction. Many reports on halogen bond interactions have been published thus far, but many of them discuss halogen bond in the context of crystal engineering or supramolecular architecture. Since a seminal report by Bolm in 2008, halogen bond-assisted or -promoted organic synthesis has received significant attention. This review aims to introduce the molecular design of suitable halogen bond donors and organic transformations involving halogen bond interactions to afford a variety of organic compounds.

2018年

18. フッ素系発光材料


山田重之*,久保田俊夫* 『有機フッ素化合物の最新動向』(シーエムシー出版,今野 勉 監修), 第3章2節 (ISBN: 978-4-7813-1337-5).


17. テトラフルオロエチレン基を有する有機分子の合成開発


今野勉* 『有機フッ素化合物の最新動向』(シーエムシー出版,今野 勉 監修), 第1章6節 (ISBN: 978-4-7813-1337-5).


16. New Types of Negative Dielectric Anisotropy Liquid Crystals: Synthesis of CF2CF2-Carbocyclic Mesogens and an Evaluation of Their Liquid Crystal Characteristics


Shigeyuki Yamada, Tsutomu Konno* Chemical Elements (Fluorine, Rhodium and Rubidium): Properties, Synthesis and Applications, Section I, Chapter 2 (Nova Science Publishers) (ISBN: 978-1-53614-018-7).

2015年

15. (R)-4,4,4-Trifluoro-1,3-diphenylbutan-1-one


今野 勉* フッ素化学入門 2015, フッ素化合物の合成法, 2015, 265–268 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0727-2).

14. Diethyl (3,3,3-Trifluoroprop-1-yn-1-yl)phosphonate


今野 勉* フッ素化学入門 2015, フッ素化合物の合成法, 2015, 273–277 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0727-2).


13. (2S,3S)- and (2S,3R)-2-Benzyloxy-4,4,5,5-tetrafluorohept-6-en-3-ol


今野 勉* フッ素化学入門 2015, フッ素化合物の合成法, 2015, 295–300 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0727-2).

12. 3,3,4,4,5,5-Hexafluoro-1,2-diphenylcyclopentene and 2,3,3,4,4,5,5-heptafluoro-1-phenylcyclopentene


今野 勉*,山田重之 フッ素化学入門 2015, フッ素化合物の合成法, 2015, 311–315 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0727-2).

11. (Z)-(1,2-Difluoroprop-1-en-1-yl) 4-methylphenyl sulfide


今野 勉* フッ素化学入門 2015, フッ素化合物の合成法, 2015, 319–321 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0727-2).

2014年

10. Trifluoromethylated Internal Alkynes: Versatile Building Blocks for the Preparation of Various Fluorine-Containinig Molecules


Tsutomu Konno*, Synlett 2014, 1350–1370 (DOI: 10.1055/s-0033-1340867)

Trifluoromethylated alkynes (CF3 alkynes) are among the most powerful synthetic intermediates for the preparation of ­fluorine-containing materials. In this account, our recent advances on the synthesis and reactions of trifluoromethylated alkynes are described.

2013年

9. Trifluoromethyl (CF3) group insertion methods in stereoselective synthesis


Tsutomu Konno*, Stereoselective Synthesis of Drugs and Natural Products (Eds. Andrunshko, V.; Andrunshko, N.), Chapter 26, John Wiley and Sons, Inc. 2013 (DOI: 10.1002/9781118596784.ssd026)

This review concerns the stereoselective construction of a trifluoromethyl (CF3)-containing multiple bond framework. In particular, synthetic methods for the preparation of multisubstituted CF3-alkenes and -allenes, including some biologically active CF3-substances, are presented. These methods are divided into two categories, such as direct trifluoromethylation and building block methodology, and they are described in detail. Synthetic methods for the preparation of trifluoromethylated alkynes as well as aromatics, which belong to materials having a multiple bond framework, but not substances prepared through stereoselective reactions, are included in this review.

2010年

8. カルボニル化合物のα位にトリフルオロメチル基を立体選択的に導入する光学活性α-トリフルオロメチルカルボニル化合物合成の最近の進歩 [最新のトピックス]


今野 勉*,石原 孝 化学 2010, 65, 66–67 (化学同人, ISSN 0451-1964)

有機分子に少数のフッ素原子を導入すると,フッ素原子がもつ性質 (最大の電気陰性度,水素に次いで小さな原子半径,大きなC–F結合エネルギーなど) に起因して,特異な機能がしばしば分子に付与される。こうした理由から現在では,化合物の分子修飾法の一つとして,フッ素原子導入が広く認識されるようになった。

7. Stereoselective Construction of an Asymmetric Carbon Center Posssessing a Trifluoromethyl Group


Tsutomu Konno* Current Organic Chemistry, Bentham Science, 2010, 7, 455–493 (DOI: 10.2174/157017910792246072)

Stereoselective synthetic methods for the construction of the tertiary or quaternary asymmetric carbon centers having a trifluoromethyl group and carbon substituent(s) or hydrogen atom, not heteroatom substituent(s), are described.

6. 有機フッ素化学基礎,含フッ素合成素子を用いる方法


今野 勉* フッ素化学入門 2010 基礎と応用の最前線, 2010, 104–152 (独立行政法人 日本学術振興会・フッ素化学第155委員会 編, 三共出版) (ISBN: 978-4-7827-0628-2).

2006年

5. Recent Advances in the Chemistry of Fluorine-Containing π-Allylmetal and Allenylmetal Complexes


Tsutomu Konno*, Takashi Ishihara, Advances in Organic Synthesis: Modern Organofluorine Chemistry - Synthetic Aspects (Eds. Atto-Ur-Rahman, Kenneth K. Laali), Bentham Publishing House, 2006, 2, 491–522 (DOI: 10.2174/97816080519841060201).

π-Allylmetal complexes derived from α-fluoroalkylated allyl mesylates react smoothly with various nucleophiles such as stabilized carbanions, carboxylates, and amines at the carbon distal to a fluoroalkyl group in a highly regioselective manner to give the corresponding γ-products in high to excellent yields. Treatment of the above fluorine-containing π-allylmetal complexes with hydride nucleophile gives the adducts derived from the hydride attacking on the carbon attached to a fluoroalkyl group. The γ-adducts, obtained by the reaction of π-allylpalladium complex with α-methoxy acetate or N-protected glycine, undergo smooth Ireland-Claisen rearrangement to give the corresponding multifunctionalized molecules in high yields. On the other hand, the reaction of α- fluoroalkylated propargylic mesylates with zinc reagents or stabilized carbanions in the presence of palladium catalyst affords fluorine-containing allene or furan derivatives respectively, in high yields, via allenylpalladium complex.

4. α-Fluorostylene


Tsutomu Konno*, e-EROS, Encyclopedia of Reagents for Organic Synthesis 2005, RN00627 (DOI: 10.1002/047084289X.rn00627).

3. 1-(3,3,3-Trifluoroprop-1-ynyl)benzene


Tsutomu Konno*, e-EROS, Encyclopedia of Reagents for Organic Synthesis 2005, RN00626 (DOI: 10.1002/047084289X.rn00626).

2. シグマトロピー転位反応を基盤とした光学活性含フッ素有用合成素子の創出


今野 勉*,有機合成化学協会誌(総合論文), 2005, 63, 26–39 (有機合成化学協会, ISSN 0037-9980).

Optically active γ-fluoroalkylated allylic alcohols were prepared via various synthetic protocols such as enzymatic resolution of the racemate, difluorocarbene-mediated reaction, and a novel 1,3-allylic rearrangement of α-fluoroalkylcarbinols. Thus-obtained allylic alcohols could participate nicely in various sigma tropic rearrangements such as Johnson-, Eshenmoser-, Ireland-Claisen, and [2,3]-Wittig shifts, to give the corresponding rearranged products with excellent stereoselectivity in good to high yields. The sequential operation of 1,3-allylic shift and the following Ireland-Claisen rearrangement realized the one-pot synthesis of the multifunctionalized building blocks in high yields from easily accessible α-fluoroalkylated cardinals. The Ireland-Claisen products underwent iodolactonization and osmylation, γ-lactones with four successive chiral centers being afforded in a highly stereoselective manner.

1. A New Aspect of Fluoroalkylated Acetylenes: Synthesis and Applications – Hydrometallation and Carbometallation


Tsutomu Konno*, Takashi Ishihara, Fluorine-Containing Synthons (Eds. Vadim A. Soloshonok) ACS Publications, Oxford University Press, 2005, 190–203 (DOI: 10.1021/bk-2005-0911.ch009).

The facile and practical syntheses of various fluorine-containing alkynes are described. Thus-obtained alkynes undergo smooth hydrostannation, hydroboration, carbo-stannylation, and carbocupration reactions to afford the corresponding hydro- and carbo-metallated adducts in a highly regio- and stereoselective manner. With this synthetic methodology, a short total synthesis of estrogen-dependent antitumor agent, panomifene has been realized.