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Development of catalytic fluorination reactions based on sigma-bond metathesis

Research Project

Project/Area Number 26410045
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Kuniyasu Hitoshi  大阪大学, 工学研究科, 准教授 (00252594)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsヒドロフッ素化 / カルボフッ素化 / アルキン / エポキシド / σボンドメタセシス / ヒドロフッソ化 / 銅触媒
Outline of Final Research Achievements

This project was focused on the development of fluorination reaction using safe and cheap fluorinating reagents. The developed catalytic fluorination reactions are as follows. (1) By reacting allene with aryl iodides and cesium fluoride in the presence of a palladium catalyst, the addition reaction of aryl group and fluorine proceeded. (2) By reacting alkyne with benzoyl fluoride and a tertiary alcohol in the presence of a copper catalyst, hydrofluorination reaction took place to give fluorinated alkene derivatives. (3) By treating the epoxide with benzoyl fluoride in the presence of a copper catalyst, aroylfluorination of epoxides occurred to yield fluorinated esters via C-O bond cleavage.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (46 results)

All 2017 2016 2015

All Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (40 results) (of which Int'l Joint Research: 3 results) Book (1 results)

  • [Journal Article] Nickel-Catalyzed Dimerization and Alkylarylation of 1,3-Dienes with Alkyl Fluorides and Aryl Grignard Reagents2016

    • Author(s)
      Takanori Iwasaki, Xin Min, Asuka Fukuoka, Hitoshi Kuniyasu, and Nobuaki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 18 Pages: 5550-5554

    • DOI

      10.1002/anie.201601126

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fe-Catalyzed Cross-Coupling Reaction of Vinylic Ethers with Aryl Grignard Reagents2016

    • Author(s)
      Takanori Iwasaki, Ryo Akimoto, Hitoshi Kuniyasu, and Nobuaki Kambe
    • Journal Title

      Chem. Asian J.

      Volume: 11 Issue: 20 Pages: 2834-2837

    • DOI

      10.1002/asia.201600972

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Multicomponent Coupling Reaction of Perfluoroarenes with 1,3-Butadiene and Aryl Grignard Reagents Promoted by an Anionic Ni(II) Complex2016

    • Author(s)
      Takanori Iwasaki, Asuka Fukuoka, Xin Min, Wataru Yokoyama, Hitoshi Kuniyasu, and Nobuaki Kambe
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 19 Pages: 4868-4871

    • DOI

      10.1021/acs.orglett.6b02343

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Cis Insertion of DMAD into Au-P Bonds: Effect of Auxialiary Ligands on the Reaction Mechanism2015

    • Author(s)
      Hitoshi Kuniyasu, Takuya Nakajima, Takashi Tamaki, Takanori Iwasaki, Nobuaki Kambe
    • Journal Title

      Organometallics

      Volume: 34 Issue: 7 Pages: 1373-1376

    • DOI

      10.1021/acs.organomet.5b00078

    • Related Report
      2015 Research-status Report 2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] (4)Cu-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents2015

    • Author(s)
      Takanori Iwasaki, Ryohei Shimizu, Reiko Imanishi, Hitoshi Kuniyasu, and Nobuaki Kambe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 127 Issue: 32 Pages: 9479-9482

    • DOI

      10.1002/ange.201503288

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] ニッケル触媒を用いたパーフルオロアレーン、アリールグリニャール試薬、1,3-ブタジエンの多成分反応とその機構研究2017

    • Author(s)
      横山航、福岡明日香、閔欣、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川(慶應義塾大学 日吉キャンパス)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] コバルト触媒によるフッ化アルキルとアルキルグリニャール試薬とのクロスカップリング反応2017

    • Author(s)
      山下晃司、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川(慶應義塾大学 日吉キャンパス)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ニッケル触媒によるパーフルオロアレーン、アリールグリニャール試薬、1,3-ブタジエンとの多成分反応2016

    • Author(s)
      横山航、福岡明日香、閔欣、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      第25回石油学会関西支部第61回日本エネルギー学会関西支部合同研究発表会
    • Place of Presentation
      京都(京都大学桂キャンパス)
    • Year and Date
      2016-12-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] ハロゲン化アルキルによるアレン類のアルキル化反応2016

    • Author(s)
      佐々木惟莉亜、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      第25回石油学会関西支部第61回日本エネルギー学会関西支部合同研究発表会
    • Place of Presentation
      京都(京都大学桂キャンパス)
    • Year and Date
      2016-12-09
    • Related Report
      2016 Annual Research Report
  • [Presentation] Nickel-Catalyzed Multicomponent Coupling Reaction of 1,3-Dienes2016

    • Author(s)
      Takanori Iwasaki, Xin Min, Asuka Fukuoka, Wataru Yokoyama, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The 10th International Symposium on Integrated Synthesis (ISONIS-10)
    • Place of Presentation
      Hyogo
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] 酸フルオリドをフッ素源とするエポキシドの触媒的アロイルフッ素化反応2016

    • Author(s)
      塩崎大悟、国安均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      東京(タワーホール船堀)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Nickel-catalyzed multicomponent reaction of perfluoroarenes, aryl Grignard reagents, and two molecules of 1,3-butadiene2016

    • Author(s)
      Wataru Yokoyama, Asuka Fukuoka, Xin Min, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      International Symposium on C-O Activation (ISCO 2016)
    • Place of Presentation
      Hyogo
    • Year and Date
      2016-10-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Co-catalyzed cross-coupling reaction of alkyl fluorides with alkyl Grignard reagents2016

    • Author(s)
      Koji Yamashita, Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      International Symposium on C-O Activation (ISCO 2016)
    • Place of Presentation
      Hyogo
    • Year and Date
      2016-10-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ニッケル触媒による1,3-ブタジエンの二量化を伴ったパーフルオロアレーン、アリールグリニャール試薬、1,3-ブタジエンとの多成分反応2016

    • Author(s)
      横山航、福岡明日香、閔欣、岩﨑孝紀、国安 均、神戸宣明
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      東京(早稲田大学西早稲田キャンパス)
    • Year and Date
      2016-09-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 酸フルオリドをフッ素源とするエポキシドの触媒的アロイルフッ素化反応2016

    • Author(s)
      塩崎大悟、国安均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      東京(早稲田大学西早稲田キャンパス)
    • Year and Date
      2016-09-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] Nickel-Catalyzed Multicomponent Reaction of Perfluoroarenes, Aryl Grignard Reagents, and 1,3-Butadiene through Dimerization of 1,3-Butadiene2016

    • Author(s)
      Wataru Yokoyama, Asuka Fukuoka, Xin Min, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      20th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Kyoto
    • Year and Date
      2016-07-10
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Co-Catalyzed Cross-Coupling Reaction of Alkyl Fluorides with Tertiary Alkyl Grignard Reagents2016

    • Author(s)
      Koji Yamashita, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      20th International Symposium on Homogeneous Catalysis
    • Place of Presentation
      Kyoto
    • Year and Date
      2016-07-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] 酸フルオリドをフッ素源とするエポキシドの触媒的フッ素化反応2016

    • Author(s)
      塩崎大悟、国安均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      第5回JACI/GSCシンポジウム
    • Place of Presentation
      兵庫(ANAクラウンプラザホテル神戸)
    • Year and Date
      2016-06-03
    • Related Report
      2016 Annual Research Report
  • [Presentation] 銅触媒を用いた共役ジエン類のヒドロ及びアルキルパーフルオロアリール化反応2016

    • Author(s)
      岡本華奈子、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 酸フルオリドをフッ素源として用いた銅触媒によるフッ素化反応2016

    • Author(s)
      塩崎大悟、国安均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル触媒を用いた1,3-ブタジエンの二量化を伴うパーフルオロアレーンとアリールグリニャール試薬との多成分反応2016

    • Author(s)
      閔欣、福岡明日香、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル触媒によるアルキル-アルキルクロスカップリング反応を利用したシクロプロパン含有脂肪酸の合成2016

    • Author(s)
      寺東祥平、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Anionic Group 9 Transition Metal Complexes: Structure and Reactivities2016

    • Author(s)
      Takanori Iwasaki, Hiroaki Takagawa, Kanako Okamoto, Suruya Prakash Singh, Yoshinori Miyata, Ryo Akimoto, Yuuki Fujii, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      Biotechnology and Chemistry for Green Growth
    • Place of Presentation
      大阪大学 (大阪府吹田市)
    • Year and Date
      2016-03-09
    • Related Report
      2015 Research-status Report
  • [Presentation] Ni-catalyzed dimerizative alkylarylation of 1,3-butadiene by alkyl halides and aryl Grignard reagents2015

    • Author(s)
      Takanori Iwasaki, Asuka Fukuoka, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)2015

    • Author(s)
      Xin Min, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Cu-catalyzed Hydro- and Alkylperfluoroarylation of 1,3-Butadiene2015

    • Author(s)
      Kanako Okamoto, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] The Copper-Catalyzed Hydrofluorination of alpha, beta Acetylenic Estersand Aroylfluorination of Epoxides2015

    • Author(s)
      Daigo Shiozaki, Hitoshi Kuniyasu, Masato Nakazaki, Takanori Iwasaki, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of cyclopentadienyl rhodium complexes bearing a cyclodextrin and their application to catalytic reactions2015

    • Author(s)
      Hiroki Yamauchi, Susumu TSUDA, Takanori Iwasaki, Shin-ichi Fujiwara, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Regioselective cis insertion of DMAD into Au-P bonds: Effect of auxiliary ligands on reaction mechanism2015

    • Author(s)
      Takuya Nakajima, Hitoshi Kuniyasu, Takashi Tamaki, Takanori Iwasaki, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Rhodium-catalyzed arylation of vinyl ethers with Grignard reagents and its mechanistic studies using a flow micro reactor2015

    • Author(s)
      Takanori Iwasaki, Ryo Akimoto, Yoshinori Miyata, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Nickel-Catalyzed Multi-Component Coupling Reaction of Perfluoroarenes, Alkyl Grignard Reagents, and 1,3-Butadiene2015

    • Author(s)
      Xin Min, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The Eighth International Forum on Chemistry of Functional Organic Chemicals (IFOC-8)
    • Place of Presentation
      東京大学弥生講堂一条ホール (東京都文京区)
    • Year and Date
      2015-11-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Copper-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents2015

    • Author(s)
      Takanori Iwasaki, Ryohei Shimizu, Reiko Imanishi, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      リーガロイヤルホテル京都 (京都府京都市)
    • Year and Date
      2015-11-09
    • Related Report
      2015 Research-status Report
  • [Presentation] 銅触媒による1,3-ジエンの位置選択的ヒドロアルキル化反応2015

    • Author(s)
      岩﨑孝紀、清水良平、今西怜子、国安 均、神戸宣明
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場(東京都新宿区)
    • Year and Date
      2015-11-05
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル触媒による二量化を伴った1,3-ブタジエンのヒドロパーフルオロアリール化反応2015

    • Author(s)
      閔欣、岩﨑孝紀、国安 均、神戸宣明
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] Pd/Xantphos触媒存在下、CsF/ArI/18-crown-6を用いるアレン類のアリールフッ素化反応2015

    • Author(s)
      中島拓耶、國安 均、若狭崇志、真川敦嗣、岩﨑孝紀、神戸宣明
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] Au-PPh3結合間へのDMADのシス挿入反応2015

    • Author(s)
      中島拓耶、國安 均、玉置喬士、岩﨑孝紀、神戸宣明
    • Organizer
      錯体化学会第65回討論会
    • Place of Presentation
      奈良女子大学(奈良県奈良市)
    • Year and Date
      2015-09-21
    • Related Report
      2015 Research-status Report
  • [Presentation] 銅触媒存在下、ベンゾイルフルオリドをフッ素源とするα,β-アセチレニックエステルのヒドロフッ素化反応およびエポキシドのベンゾイルフッ素化反応2015

    • Author(s)
      塩崎大悟、国安均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] 鉄触媒を用いたアルケニルエーテルとグリニャール試薬とのクロスカップリング反応2015

    • Author(s)
      秋本諒、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル触媒による1,3-ブタジエンの二量化を伴うパーフルオロアレーンとアルキルグリニャール試薬との反応2015

    • Author(s)
      閔欣、岩﨑孝紀、国安均、神戸宣明
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規な環状分子の合成を目指したシクロデキストリン誘導体の合成と反応2015

    • Author(s)
      倉田周弥、岩﨑孝紀、国安 均、神戸宣明
    • Organizer
      第48回有機金属若手の会 夏の学校
    • Place of Presentation
      白浜荘(滋賀県高島市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 銅触媒を用いたエポキシドのアロイルフッ素化反応2015

    • Author(s)
      塩崎大悟、国安 均、中﨑雅人、岩﨑孝紀、神戸宣明
    • Organizer
      第48回有機金属若手の会 夏の学校
    • Place of Presentation
      白浜荘(滋賀県高島市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
  • [Presentation] シクロプロパン環を有するビルディングブロックの合成とクロスカップリング反応への応用2015

    • Author(s)
      寺東祥平、岩﨑孝紀、国安 均、神戸宣明
    • Organizer
      第48回有機金属若手の会 夏の学校
    • Place of Presentation
      白浜荘(滋賀県高島市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 2級アルコールの塩化チオニルによるハロゲン化における添加剤の効果2015

    • Author(s)
      山北雄一、岩﨑孝紀、国安 均、神戸宣明
    • Organizer
      第48回有機金属若手の会 夏の学校
    • Place of Presentation
      白浜荘(滋賀県高島市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 遷移金属触媒による1,3-ブタジエンのパーフルオロアリール化2015

    • Author(s)
      岩﨑孝紀、閔欣、岡本華奈子、福岡明日香、国安 均、神戸宣明
    • Organizer
      石油学会第58回年会第20回JPIJSポスターセッション
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-05-26
    • Related Report
      2015 Research-status Report
  • [Presentation] ニッケル触媒によるフッ化アルキル、ブタジエン、アリールグリニャール試薬との多成分反応2015

    • Author(s)
      岩﨑孝紀、福岡明日香、閔欣、国安 均、神戸宣明
    • Organizer
      第13回次世代を担う有機化学シンポジウム
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県草津市)
    • Year and Date
      2015-05-22
    • Related Report
      2015 Research-status Report
  • [Book] 化学英語101 第1版 第11刷2015

    • Author(s)
      國安 均
    • Total Pages
      181
    • Publisher
      化学同人
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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