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プラス Seminar on Green Sustainable Chemistry in …1 日本化学会中国四国支部...
Transcript of プラス Seminar on Green Sustainable Chemistry in …1 日本化学会中国四国支部...
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日本化学会中国四国支部
平成 25 年度 鳥取地区化学講演会 プラス
Seminar on Green Sustainable Chemistry in Tottori (2013-2)
日時:2013年10月25日(金) 13:20〜17:00
場所:鳥取大学大学院工学研究科大講義室
鳥取市湖山町南4-101
主催 日本化学会中国四国支部
主催 鳥取大学グリーン・サスティナブル・ケミストリー
(GSC)研究センター
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プログラム
開会挨拶 センター長 伊藤 敏幸
13:30-14: 30: 座長 伊藤 敏幸
Peter Wasserscheid (フリードリヒ・アレクサンダー大学エアラン
ゲン=ニュンベルク 教授)
「 Ionic Liquid Thin Films in Catalysis- Fundamental
Aspects and Applications」
14:30-15:30:座長 片田 直伸
秋山 隆彦(学習院大学理学部化学科 教授)
「 Recent Progress in the Chiral Phosphoric Acid
Catalyzed Reactions」
15:30-15:40 休憩
−−<鳥取地区化学講演会>−−
15:40-16:40:座長 南条 真佐人
吉田 勝(産業技術総合研究所 ナノテクノロジー・材料・製造分野研究
企画室長)
「 Gels and Photoresponsive Compounds As Novel
Smart Materials」
閉会
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Takahiko Akiyama Takahiko Akiyama was born in Kurashiki, Okayama, Japan, in 1958. He received his PhD in 1985 from the University of Tokyo. After working at the Shionogi Research Laboratories, Shionogi & Co., Ltd, as a research chemist, he was appointed as an Assistant Professor at Ehime University in 1988. He worked with Professor Barry M. Trost as a visiting scholar at Stanford University in 1992-1993 and moved to Gakushuin University as an Associate Professor in 1994. He has been a Professor of Chemistry at Gakushuin University since 1997. He is the recipient of the Chemical Society of Japan Award for Creative Work (2009), Daiichi-Sankyo Award for Medicinal Organic Chemistry (2009), and Nagoya Silver Medal (2012). His current research interests are development of new and useful synthetic methodologies based on the design of novel chiral Brønsted acid catalysts as well as the utilization of transition metal catalysts.
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Recent Progress in the Chiral Phosphoric Acid Catalysis
Takahiko Akiyama Department of Chemistry, Faculty of Science, Gakushuin University,
1-5-1 Mejiro, Toshima-ku, Tokyo, 178-8588, Japan E-mail: [email protected]
URL: http://www-cc.gakushuin.ac.jp/~940020/akiyama_site/ Abstract
Development of efficient chiral catalyst constitutes an important area in the fields of organic chemistry. We synthesized chiral cyclic phosphoric acid 1, starting from (R)-BINOL, and demonstrated its catalytic activity in the nucleophilic addition and cycloaddition toward imines.1 We wish to discuss recent progress in the chiral phosphoric acid catalyzed reactions.
Enantioselective reduction of ketimines constitutes an important method for the preparation of amines in optically pure form. We have found that benzothiazoline proved to be efficient hydrogen donor in combination with chiral phosphoric acid in the transfer hydrogenation of ketimines to furnish the corresponding amines with high to excellent enantioselectivities.2
Multi-substituted chiral biaryls were obtained with excellent enantioselectivity by enantioselective bromination of Cs-symmetric biaryls by use of N-bromophthalimide.3
1) a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566-1568. b) Akiyama, T. Chem. Rev. 2007, 107, 5744-5758.
2) Zhu, C.; Akiyama, T. Org. Lett. 2009, 11, 4180-4183. b) Zhu, C.; Akiyama, T. Adv. Synth. Catal. 2010, 352, 1846–1850. c) Henseler, A.; Kato, M.; Mori, K.; Akiyama, T. Angew. Chem. Int. Ed. 2011, 50, 8180–8183. d) Saito, K.; Akiyama, T. Chem. Commun. 2012, 48, 4573-4575.
3) Mori, K.; Ichikawa, Y.; Kobayashi, M.; Shibata, Y.; Yamanaka, M.; Akiyama, T. J. Am. Chem. Soc. 2013, 135, 3964–3970.
O
OPO
X
X
O
H
1
R1 R2
NHPMP
S
HN
Ar
Ar CF3
HN PMP
95-98% eeAr CO2Me
HN PMP
93-99% eeAr CH3
HN PMPH2
95-98% ee
R1 R2
N PMP+
1
+
HO OHR3O
OR2
R1
HO OHR3O
OR2
R1
Br
N
O
O
Br1
80-91%, 82-98% ee
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Masaru Yoshida Masaru Yoshida was born in Ofunato, Iwate, Japan, in 1966. He received his B. Sc. in 1989 and Dr. Sc. in 1994 from Tohoku University under the direction of the Professor Hideki Sakurai. After that, he joined National Institute of Chemical and Materials Research (NIMC) as a Research Scientist (In 2001, NIMC was reorganized to be National Institute of Advanced Industrial Science and Technology (AIST)). He joined Professor Jean M. J. Fréchet’s group at UC Berkeley as a Visiting Scholar in 2002-2004 with a financial support of the JSPS fellowship. During 2006-2007, he worked for Council for Science and Technology Policy, Cabinet Office as an inspector. In 2008, he was promoted to be Group Leader in Nanotechnology Research Institute in AIST. In 2013, he moved on to be Director of Research Planning Office for Nanotechnology, Materials and Manufacturing in AIST. In 2013, he received Commendation for Science and Technology by the Minister of Education, Culture, Sports, Science and Technology due to the discovery of the photochemically reversible liquefaction and solidification phenomena of single compounds under isothermal conditions. His research interest is in “smart” materials including gels, polymers and liquid crystals with stimuli-responsibility.
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Gels and Photoresoponsive Compounds as Novel Smart Materials
Masaru Yoshida Research Planning Office for Nanotechnology, Materials and Manufacturing,
National Institute of Advanced Industrial Science and Technology (AIST), Central 2, 1-1-1 Umezono, Tsukuba, Ibaraki 305-8568, JAPAN
E-mail: [email protected]
Abstract We have investigated linear oligomeric and
polymeric electrolytes with both ammonium and benzamide backbones can undergo physical gelation as ionic gelators.1 Herein, we report a novel ionic gel-forming polyelectrolyte that efficiently and specifically works for the ionogel preparation using a variety of ionic liquids.2 It is a polymer with N,N′- (trans-cyclohexane-1,4-diyl)dibenzamide linkages as the key structural moieties and is shown as CDBA6·X in Chart 1, where X represents a monoanion that is either chloride, bis(trifluoromethanesulfonyl)amide (TFSA), or bis(fluorosulfonyl)amide (FSA). It was found that CDBA6·X specifically led to the formation of a variety of physical gels of ILs at concentrations that are lower than that of the conventional gelators. We also report novel photoreactive molecular systems based on stilbene and azobenzene, including photochemically tunable dispersant for carbon nanotubes in aqueous solution3 and the first example of photochemically reversible liquefaction and solidification of single compounds under strictly isothermal conditions.4,5
1) M. Yoshida, N. Koumura, Y. Misawa, N. Tamaoki, H. Matsumoto, H. Kawanami, S. Kazaoui and N. Minami, J. Am. Chem. Soc. 2007, 129, 11039-11041. 2) J. Nagasawa, H. Matsumoto, M. Yoshida, ACS Macro Letters 2012, 1, 1108-1111. 3) Y. Matsuzawa, H. Kato, H. Ohyama, D. Nishide, H. Kataura, M. Yoshida, Adv. Mater. 23, 3922-3925 (2011). 4) Y. Norikane, Y. Hirai, M. Yoshida, Chem. Commun. 2011, 47, 1770-1772. 5) H. Akiyama, M. Yoshida, Adv. Mater. 2012, 24, 2353-2356.
Chart 1. Structure of CDBA6·X
Figure 1. Photographs of a 50 g/L
CDBA6·TFSA/[EMI][TFSA] ionogel. The gel size
is 6 × 6 × 18 mm.
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鳥取大学GSCセミナーの歴史
○第1回(Seminar on Green and Sustainable Chemistry in Tottori),日本化学会・グリ
ーンケミストリー研究会(17th Green Chemistry Forum)と共催,平成20年12月10日,
とりぎん文化会館(鳥取県民文化会館)小ホール, 講師3名,出席者187名
講師:上村明男(山口大学大学院医学系研究科 教授),「プラスチックの化学リサイクルに向けた
新しい方法」
講師:丹羽 幹(鳥取大学大学院工学研究科 教授),「Yゼオライトのブレーンステッド酸性質発
現と触媒活性」
講師:萩原久大(新潟大学大学院自然科学研究科 教授)「イオン液体固定化触媒(SILC)とグリ
ーンケミストリー」
講師: Professor TECK PENG LOH(Nanyang Technological University,(Singapore))
“Ionic Liquids as Green Solvents & Catalysts for Organic Synthesis”
○第2回(Seminar on Green and Sustainable Chemistry in Tottori 2009 (1))(科研費,
特定領域研究「イオン液体の科学」,触媒学会,石油学会と共催),H21年11月14日,工学
研究科大講義室,講師13名,出席者167名
講師:Professor Douglas MacFarlane( Monash Univ., Australia)” Ionic Liquids and
Global Sustainability”
講師:Dr. Asako Narita (Kyoto University, Japan) “Ionic Liquid-modified Inorganic
Nanoparticles and their Biomedical Applications”
講師:Dr. Hideo Midorikawa (Asahi Kasei Chemicals Corp., Japan), “Environmental
Friendly Process for Producing Cyclohexanol from Benzene by Using Heterogeneous
Catalysts”
講 師 : Dr. Kazu Okumura (Tottori Univ., Japan), “In situ X-ray Absorption
Spectroscopic Study of Highly Dispersed Pd Species Active in the Suzuki-Miyaura
Reactions”
講師:Professor Toshiyuki Itoh (Tottori Univ., Japan), “Iron Salt-catalyzed One-Pot
Nazarov Cyclization / Michael Reaction of Pyrrole Derivatives
講師:Professor Bohari M. Yamin (Univ. Kebangsaan, Malaysia), “Structural and
Complexation Studies of Fluorophenylthioureas”
講師:Dr. Hyunjoo Lee (KIST, Korea),” Alkyl Polyfluoroalkyl Imidazolium Ionic liquids:
Synthesis and Characterization”
講師:Dr. Hisashi Shimakoshi (Kyushu Univ., Japan), “Bio-related Tetrapyrrole Catalyst
with Ionic Liquid”
講 師 : Professor Kenji Takahashi, (Kanazawa Univ., Japan),” ormation of
Anhydrosugars from Cellobiose in Ionic Liquids”
講師:Dr. Mayumi Nishida (Koei Chemical Co. Ltd., Japan), ” The Development of
Koei’s Ionic Liquids”
講師:Professor Seiji Suga, (Okayama Univ., Japan), ” Electroorganic Synthesis Using
Micro Reaction Systems”
講師:Professor Toshio Fuchigami (Tokyo Institute of Technology, Japan),” Highly
Selective Fluorination of Organic Molecules and Macromolecules in Ionic Liquids”
講師:Professor Junko N. Kondo (Tokyo Institute of Technology, Japan), “Crystalline
Mesoporous Ta2O5 Photocatalyst for Overall Water Splitting”
○第3回(Seminar on Green and Sustainable Chemistry in Tottori 2009 (2))H21年
12月1日,工学研究科代講義室, 講師2名,出席者154名
講師:Professor Pedro Lozano (University of Murcia, Spain), “Enzymatic Catalysis in
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Ionic Liquids and sc-CO2 Biphasic Systems”
講師:Professor Joe Chappell University of Kentucky, USA),“Evolving the Catalytic (
Specificity of Terpene Biosynthetic Enzymes and the Development of Sustainable,
Robust Production Platforms in Yeast and Plants”
○第4回(2010年度GSC in Tottori(1))(日本化学会,第53回中国四国産学連携化学フ
ォーラムと共同開催)H22年9月20日,工学研究科大講義室,講師5名,出席者177
特別講演: J-E. Bäckvall(ストックホルム大学教授)” A Biomimetic Approach to Green Organic Transformations”
特別講演: B. K. Mihovilovic(ウイーン工業大学教授)“Bioorganic Chemistry in Sustainable
Synthesis”
講師:國信洋一郎(岡山大学大学院自然科学研究科 助教)「不活性結合の切断を鍵とする新規有
機合成反応の開発」
講師:米山公啓(広島大学大学院工学研究科 助教)「安全・安価な金属触媒を活用した有機合成
反応」
講師:依馬 正(岡山大学大学院自然科学研究科 准教授)「多重水素結合部位を有するキラル大環
状化合物の不斉識別機能」
○第5回(2010年度GSC in Tottori (2))(日本化学会,触媒学会,石油学会,化学工学会と
共催),H22年11月13日工学研究科大講義室,講師4名,出席者188名
講師:Suk Bong HONG (Pohang University of Science and Technology, Korea)
“Zeolite Syntheses via a CDM Approach”
講師:Shinji INAGAKI (Toyota Central R&D Labs, Inc., Japan)
“Synthesis of Optically Active Periodic Mesoporous Organosilicas toward the
Construction of Artificial Photosynthesis”
講師: Akira MIYAMOTO (Tohoku University, Japan)
“Multi-level Computational Chemistry Methods for Green and Sustainable
Chemistry”
講師: German SASTRE (Instituto de Tecnologia Quimica UPV-CSIC, Spain)
“Synthesis of Octahedral Metal Oxides with Pore Structures”
○第6回(2010年度GSC in Tottori(3)),(第1回イオン液体討論会(イオン液体研究会)
と共催)
平成23年1月17日,18日,とりぎん文化会館,参加者186名
特別講演:R. Rogers(アラバマ大学 教授,米国)“Ionic Liquid Solvents for the Grand
Challenge Inherent in a Biorefinery: Extraction and Separation of Lignin, Cellulose, and
Hemicellulose” 特別講演:M-J. KOO(インハ大学 教授,韓国,韓国生物工学会会長)“Application of
Ionic Liquids in Bioconversion Process”
○第7回(2011 Green Sustainable Chemistry Seminar in Tottori (1))
2011年12月15日(木),共通教育棟A20講義室,出席者93名,講師3名
講師:久枝良雄 (九州大学大学院工学研究院 教授)「Bio-inspired Catalysts for Degradation
of Environmental Pollutants: Lessons from Metalloenzyme(バイオインスパイアード触媒
の創製と環境浄化への応用)」
講師:稲永純二 (九州大学先導物質化学研究所 教授)「Green Asymmetric Catalysis with
Diionic Chiral Sc-Complex in Ionic Liquid: An Organic Solvent-Free Catalytic
Asymmetric Reaction Process(有機溶媒フリーの不斉反応プロセスの構築)」
講師:Suojiang Zhang (中国科学院(北京)教授,プロセス工学研究所長)「Hydrogen Bonds:
A New Insight Into Ionic Liquids」
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○第8回(2011 Green Sustainable Chemistry Seminar in Tottori (2))
2012年2月14日(火曜),工学研究科大講義室,出席者193名,講師3名
講師:小川 順(京都大学大学院農学研究科 教授)「Valuable microbial functions pioneering
bio-based industry- development of bio-lipid platform and biotransformation 」
講師:酒井貴志(岡山大学大学院自然科学研究科 教授)「New and Efficient Catalysts for
Activation of Carbon Dioxide and Epoxide to Produce Cyclic Carbonate」
講師:Xin-Hui Xing(中国,清華大学 教授)「Microbial Evolution Engineering for Microbial
Strain Improvement」
○第9回(2012 Green Sustainable Chemistry Seminar in Tottori (1))
GSC研究センター設置記念講演会
2012年10月14日(火曜),共通教育棟A20講義室,出席者152名,講師3名
講師:奥村 和(鳥取大学大学院工学研究科 准教授)
「Structure and catalysis of layered NbW oxide catalysts constructed by the
self-assembly of nanofibers」
講師:Dae Yoon Chi(韓国 Sogang大学 教授)
「 New Concept Nucleophilic Fluorination Assisted by 1H-1,2,3-Triazol-3-ium
Triflates」
講師:吉田 潤一(京都大学大学院工学研究科 教授)
「空間で時間を制御する合成化学」
○第10回(2012 Green Sustainable Chemistry Seminar in Tottori (2))
2012年12月3日(月曜),工学研究科大講義室,出席者156名,講師3名
講師:Franz Hollmann (オランダ,Delft 工科大学 准教授)「Oxidoreductases for a greener
organic synthesis – scope and challenges」
講師:伊藤 伸哉(富山県立大学教授,生物工学研究センター所長)
「Development of novel biocatalysts for producing chiral compounds」
講師:溝端 知宏(鳥取大学大学院工学研究科 准教授)
「Elucidating the molecular mechanism of chaperonin- facilitated protein folding」
○第11回(2013 Green Sustainable Chemistry Seminar in Tottori(1))有機合成化
学協会中国四国支部 (第69回パネル討論会)と共催 2013年6月13日(木曜),工学研究科大講義室,出席者105名,講師3名
講師:藤井 郁雄(大阪府立大学大学院理学系研究科教授,生命環境科学域 自然科学類・学類長)
「Molecular Basis for Transition-state Stabilization in Catalytic Antibodies」
講師:宇梶 裕(金沢大学理工研究域物質化学系 教授)
「Development of novel synthetic methods for heterocycles utilizing 1,3-dipoles」
講師:三好 徳和(徳島大学大学院教授・ソシオアーツ&サイエンス研究部)
「Development and Application for Unexpected Sr-mediated Reactions」
延べ参加者1758名,講師44名