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Exploration of universal methodology for high activity and insoluble catalyst development

Research Project

Project/Area Number 15K05510
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

Yamada Yoichi M. A.  国立研究開発法人理化学研究所, 環境資源科学研究センター, 副チームリーダー (50317723)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords高分子金属触媒 / 高分子触媒 / 高活性 / 再利用性 / クロスカップリング / 鈴木-宮浦反応 / パラジウム触媒 / パラジウム / 高分子ピリミジン / 水素化 / 溶媒選択性 / 固定化触媒 / 不溶性触媒 / C-Hアリール化 / 再利用 / C-H結合活性化反応
Outline of Final Research Achievements

In order to develop a novel highly active insoluble supramolecular polymer - palladium catalyst, preparation of highly hydrophilic - lipophilic chain polypyrimidine was investigated. A polymer pyrimidine having a pentyl group, a methyl group, and a proton introduced into the main chain polymer was prepared. As a result of examining the molecular convolution of this polymer and ammonium palladate, we succeeded in the creation of a supramolecular polymer pyrimidine-palladium catalyst which is insoluble in both water and organic solvent.
This catalyst is effective for the Suzuki-Miyaura reaction with phenyl boronic acid based on a variety of aryl chlorides having low reactivity. The reaction proceeds efficiently in water with a catalytic amount of 400 mol ppm Pd.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (54 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (9 results) Journal Article (12 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 12 results,  Open Access: 3 results,  Acknowledgement Compliant: 7 results) Presentation (31 results) (of which Int'l Joint Research: 10 results,  Invited: 12 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results)

  • [Int'l Joint Research] アリストテレス大学(ギリシャ)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] Hanyang University/Seoul National University(韓国)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] Taiwan Normal University(台湾)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] Aristotle University of Thessaliniki(ギリシャ)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] Colby University(米国)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] McGill University(カナダ)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research] Hanyang University/Seoul National University(韓国)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research] Aristotle University of Thessaloniki(ギリシャ)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research] Taiwan Normal University(台湾)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Poly(meta-phenylene oxides) for the design of a tunable, efficient, and reusable catalytic platform2018

    • Author(s)
      Reuben H Hudson, Haoran Zhang, Amy LoTemplio, Georganna Benedetto, Go Hamasaka, Yoichi M. A. Yamada, Jeffrey Louis Katz, Yasuhiro Uozumi
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 23 Pages: 2878-2881

    • DOI

      10.1039/c8cc00774h

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Photocatalytic Aerobic Oxidation of Alkenes into Epoxides or Chlorohydrins Promoted by a Polymer-Supported Decatungstate Catalyst2017

    • Author(s)
      Symeonidis Theodoros S.、Athanasoulis Alexandros、Ishii Rikako、Uozumi Yasuhiro、Yamada Yoichi M. A.、Lykakis Ioannis N.
    • Journal Title

      ChemPhotoChem

      Volume: 1 Issue: 10 Pages: 479-484

    • DOI

      10.1002/cptc.201700079

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Catalytic Applications of a Triptycene-Based Monophosphine Ligand for Palladium-Mediated Organic Transformations2017

    • Author(s)
      Franco King-Chi Leung, Fumitaka Ishiwari, Yoshiaki Shoji, Tsuyoshi Nishikawa, Ryohei Takeda, Yuuya Nagata, Michinori Suginome, Yasuhiro Uozumi, Yoichi M. A. Yamada, and Takanori Fukushima
    • Journal Title

      ACS Omega

      Volume: 2 Issue: 5 Pages: 1930-1937

    • DOI

      10.1021/acsomega.7b00200

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of Batch and Flow Immobilized Catalytic Systems with High Catalytic Activity and Reusability2017

    • Author(s)
      Yoichi M. A. Yamada
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 9 Pages: 805-821

    • DOI

      10.1248/cpb.c17-00349

    • NAID

      130006038331

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Huisgen Cycloaddition with Acetylene Gas by Using an Amphiphilic Self-Assembled Polymeric Copper Catalyst2017

    • Author(s)
      Uozumi Yasuhiro、M. A. Yamada Yoichi、Yoshida Hiroshi、Ohno Aya、Sato Takuma、Mase Toshiaki
    • Journal Title

      HETEROCYCLES

      Volume: 95 Issue: 2 Pages: 715-715

    • DOI

      10.3987/com-16-s(s)57

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Asymmetric Suzuki-Miyaura Cross Coupling with Homochiral Phosphine Ligands Having Tetrahydro-1H-imidazo[1,5-a]indole Backbone2017

    • Author(s)
      Y. Uozumi, Y. Matsuura, T. Suzuka, T. Arakawa, and Y. M. A. Yamada
    • Journal Title

      Synthesis

      Volume: 49 Issue: 01 Pages: 59-68

    • DOI

      10.1055/s-0036-1589407

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] In-Water and Neat Batch and Continuous-Flow Direct Esterification and Transesterification by a Porous Polymeric Acid Catalyst2016

    • Author(s)
      H. Baek, M. Minakawa, Y. M. A. Yamada, J. Han and Y. Uozumi
    • Journal Title

      Sci. Rep

      Volume: 6 Issue: 1 Pages: 25625-25625

    • DOI

      10.1038/srep25925

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Application of Heterogeneous Polymer-Supported Catalysts to Continuous Flow Systems2016

    • Author(s)
      T. Osako, Y. M. A. Yamada and Y. Uozumi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 74 Issue: 6 Pages: 621-630

    • DOI

      10.5059/yukigoseikyokaishi.74.621

    • NAID

      130005164588

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Supramolecular Scaffold for Tailoring the Two-Dimensional Assembly of Functional Molecular Units into Organic Thin Films2016

    • Author(s)
      F. K.-C. Leung, F. Ishiwari, T. Kajitani, Y. Shoji, T. Hikima, M. Takata, A. Saeki, S. Seki, Y. M. A. Yamada, T. Fukushima
    • Journal Title

      Journal of the American Chemical Society

      Volume: 138 Issue: 36 Pages: 11727-11733

    • DOI

      10.1021/jacs.6b05513

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Production of Valuable Esters from Oleic Acid with a Porous Polymeric Acid Catalyst without Water Removal2016

    • Author(s)
      Y. -H. Kim, J. Han, B. Y. Jung, H. Baek, Y. M. A. Yamada, Y. Uozumi, and Y. -S. Lee*
    • Journal Title

      Synlett

      Volume: 27 Issue: 01 Pages: 29-32

    • DOI

      10.1055/s-0035-1560584

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Convoluted Polymeric Imidazole Palladium Catalyst: Structural Elucidation and Investigation of Driving Force for Efficient Mizoroki-Heck Reaction2015

    • Author(s)
      T. Sato, A. Ohno, S. M. Sarkar, Y. Uozumi,* and Y. M. A. Yamada*
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 14 Pages: 2141-2148

    • DOI

      10.1002/cctc.201500249

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Click Chemistry within Click Time by Polymeric Copper Membrane-Installed Microflow Catalytic Reactor2015

    • Author(s)
      Y. M. A. Yamada,* A. Ohno, T. Sato, and Y. Uozumi*
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 48 Pages: 17269-17273

    • DOI

      10.1002/chem.201503178

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 自己組織化高分子イミダゾール銅触媒によるアセチレンガスを使用したヒュスゲン環化付加2018

    • Author(s)
      大野綾、吉田兆志、佐藤太久真、間瀬俊明、魚住泰広、山田陽一
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Production of Bio Hydrofined Diesel by Hydrogenative Decarboxylation of Carboxylic Acids with Silicon Nanowire Array-Supported Rhodium Nanoparticles2018

    • Author(s)
      Heeyoel Baek, Yoichi M. A. Yamada, and Yasuhiro Uozumi
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Self-Assembled Polymeric Copper Catalyst- Promoted Huisgen Cycloaddition2018

    • Author(s)
      Yoichi M. A. Yamada, Hiroshi Yoshida, Aya Ohno, Takuma Sato, Shaheen M.Sarkar, Toshiaki mase and Yasuhiro Uozumi
    • Organizer
      IRCCS-JST CREST Joint Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] シリコンナノ構造安定化パラジウムナノ粒子:水素を用いた還元的アミノ化およびフロー合成への応用2017

    • Author(s)
      佐藤太久真、中尾愛子、魚住泰広、山田陽一
    • Organizer
      日本化学会第97回春季年会(2017)
    • Place of Presentation
      慶応大学(神奈川県日吉市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
  • [Presentation] 高活性・再利用性バッチ・フロー型固定化触媒システムの開発2017

    • Author(s)
      山田陽一
    • Organizer
      富士フローケミストリーフォーラム 2017 Spring
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] シリコンナノ構造担持パラジウムナノ粒子:アミンを基質にしたバッチ&フロー型還元的アルキル化2017

    • Author(s)
      山田陽一、佐藤太久真、中尾愛子、魚住泰広
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Instantaneous Click Chemistry Using a Copper-Containing Polymeric Membrane-Installed Microflow Device2017

    • Author(s)
      Aya Ohno, Yoichi M. A. Yamada,* Takuma Sato, and Yasuhiro Uozumi*
    • Organizer
      1th International Symposium on Integrated Synthesis (ISONIS-11) & 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] (Trans)Esterification Using a Porous Phenol-Sulfonic Acid Resin in Batch and Continuous-Flow System2017

    • Author(s)
      Heeyoel Baek, Yoichi M. A. Yamada,* Takuma Sato, and Yasuhiro Uozumi*
    • Organizer
      11th International Symposium on Integrated Synthesis (ISONIS-11) & 3rd International Symposium on Middle Molecular Strategy (ISMMS-3)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Instantaneous Huisgen Cycloaddition Using a Copper-Containing Polymeric Membrane-Installed Microflow Device2017

    • Author(s)
      Aya Ohno, Yoichi M. A. Yamada,* Takuma Sato, and Yasuhiro Uozumi*
    • Organizer
      OMCOS19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Highly Reusable Silicon Nanowire Array-Stabilized Metal Nanoparticle Catalysts for Hydrogenation2017

    • Author(s)
      Heeyoel Baek, Yoichi M. A. Yamada,* and Yasuhiro Uozumi*
    • Organizer
      OMCOS19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Silicon Nanostructure-Stabilized Palladium Nanoparticles (SiNS-Pd): Reductive Alkylation of Amines with Hydrogen and Its Application to Flow Synthesis2017

    • Author(s)
      Yoichi M. A. Yamada*,Takuma Sato, Aiko Nakao, Yasuhiro Uozumi
    • Organizer
      OMCOS19
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Silicon Nanostructure-Stabilized Palladium Nanoparticles: Reductive Amination Using H2 and Its Application to Flow Synthesis2016

    • Author(s)
      T. Sato, Y. Uozumi, and Y. M. A. Yamada
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路島(兵庫県淡路町)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Silicon Nanostructure-Stabilized Palladium Nanoparticle Catalysts for Organic Transformations2016

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      C&FC 2016 (International Symposium on Catalysis and Fine Chemicals 2016)
    • Place of Presentation
      台北(台湾)
    • Year and Date
      2016-11-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Supported Catalysts in Batch & Flow2016

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      Chemistry Seminar at Justus-Liebig-Universitat Giessen
    • Place of Presentation
      ギーセン大学(ギーセン,ドイツ)
    • Year and Date
      2016-09-09
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Highly Active, Reusable, Self-Assembled Polymeric Palladium Catalyst at Parts per Million Levels for Cross-Coupling Reactions2016

    • Author(s)
      Y. M. A. Yamada, S. M. Sarker, T. Sato, A. Ohno, and Y. Uozumi
    • Organizer
      6th International IUPAC Conference on Green Chemistry
    • Place of Presentation
      ベネチア(イタリア)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高活性な固定化触媒システムの開発2016

    • Author(s)
      山田陽一
    • Organizer
      第32回若手化学者のための化学道場(松山 2016)
    • Place of Presentation
      にぎたつ会館(愛媛県松山市)
    • Year and Date
      2016-08-25
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Highly Active and Reusable Supported Catalytic Systems: Batch & Flow2016

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      INTERNATIONAL SYMPOSIUM ON PURE & APPLIED CHEMISTRY (ISPAC) 2016
    • Place of Presentation
      Convention Centre Kuching, Kuching, Malaysia
    • Year and Date
      2016-08-17
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 医薬品合成を志向した高活性・高再利用性バッチ・フロー型固定化触媒システムの開発2016

    • Author(s)
      山田陽一
    • Organizer
      金沢大学薬学部機能性分子合成学セミナー
    • Place of Presentation
      金沢大学(石川県金沢市)
    • Year and Date
      2016-05-13
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 「医薬品合成を志向した高活性・高再利用性バッチ・フロー型固定化触媒システムの開発」2016

    • Author(s)
      山田陽一
    • Organizer
      日本薬学会学術振興賞受賞講演
    • Place of Presentation
      パシフィコ横浜(横浜市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 「シリコンナノワイヤーアレイ担持パラジウム触媒の開発」2016

    • Author(s)
      山田陽一
    • Organizer
      日本化学会年会企画講演会「天然資源としてのケイ素が鍵を握る機能性材料」
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 自己組織化高分子イミダゾールニッケル触媒によるC-N結合形成クロスカップリング2016

    • Author(s)
      石井梨夏子、大野綾、山田陽一、魚住泰広
    • Organizer
      日本化学会第96春期年会(2016)
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウムナノ粒子シリコンナノ構造複合体:常圧水素下でのアミンとアルデヒドの還元的アミノ化およびそのフロー反応への応用2016

    • Author(s)
      佐藤太久真、山田陽一、魚住泰広
    • Organizer
      日本化学会 第96春季年会 (2016)
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] 自己組織化高分子ピリジンパラジウム触媒による芳香族ハロゲン化物を用いたチオフェンの直接的アリール化反応2016

    • Author(s)
      大野綾、佐藤太久真、山田陽一、魚住泰広
    • Organizer
      日本化学会 第96春季年会 (2016)
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] "Development of a Porous Phenolsulfonic Acid Resin and Its use in Catalytic Esterification and Transesterification for Production of Biodiesel Fuels "2016

    • Author(s)
      Baek Heeyoel, Yamada M. A. Yoichi, Uozumi Yasuhiro
    • Organizer
      ACT-C 不斉炭素‐炭素結合形成反応・若手ワークショップ
    • Place of Presentation
      ホテルグランドヒル市ヶ谷(市ヶ谷、東京)
    • Year and Date
      2016-03-05
    • Related Report
      2015 Research-status Report
  • [Presentation] "Development of a silicon nanowire array-stabilized palladium nanoparticle catalyst and its application to organic reactions "2015

    • Author(s)
      Yoichi M. A. Yamada, Yoshinari Yuyama, Takuma Sato, Shigenori Fujikawa and Yasuhiro Uozumi
    • Organizer
      環太平洋国際化学会議
    • Place of Presentation
      ヒルトンホノルル(ホノルル、米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] “Supported Catalysts in Batch & Flow”2015

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      ACP Lectureship Award in Taiwan (中央研究所)
    • Place of Presentation
      中央研究所(台北、台湾)
    • Year and Date
      2015-10-08
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] “Supported Catalysts in Batch & Flow”2015

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      ACP Lectureship Award in Taiwan (国立清華大学)
    • Place of Presentation
      国立清華大学(新竹、台湾)
    • Year and Date
      2015-10-07
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] “Supported Catalysts in Batch & Flow”2015

    • Author(s)
      Yoichi M. A. Yamada
    • Organizer
      ACP Lectureship Award in Taiwan (国立中興大学)
    • Place of Presentation
      国立中興大学(台中、台湾)
    • Year and Date
      2015-09-30
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 高分子イミダゾール・パラジウム触媒:溝呂木-Heck反応と構造解析2015

    • Author(s)
      佐藤太久真、大野綾、サルカールシャヒーン、魚住泰広、山田陽一
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学(大阪府吹田市)
    • Year and Date
      2015-09-08
    • Related Report
      2015 Research-status Report
  • [Presentation] 「固定化触媒高活性化のための方法論開拓を目指して」2015

    • Author(s)
      山田陽一
    • Organizer
      大阪府立大学白鷺セミナー
    • Place of Presentation
      大阪府立大(大阪市)
    • Year and Date
      2015-06-19
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Transesterification of Various Alcohols and Esters with a Porous Phenol-Sulfonic Acid Resin2015

    • Author(s)
      Baek Heeyoel, Minakawa Maki, Yamada M. A. Yoichi, Han Jin Wook, Uozumi Yasuhiro
    • Organizer
      The 115th General Meeting 2015 of KCS
    • Place of Presentation
      ソウル、韓国
    • Year and Date
      2015-04-15
    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] 脂肪族炭化水素及び一酸化炭素の製造方法2017

    • Inventor(s)
      山田陽一,ベクヒヨル,魚住泰広
    • Industrial Property Rights Holder
      理研
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2017-111492
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] POLYARYLENE OXIDE CATALYSTS2017

    • Inventor(s)
      山田陽一ら計4名
    • Industrial Property Rights Holder
      Colby College (USA) and RIKEN
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report
    • Overseas

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Published: 2015-04-16   Modified: 2022-02-28  

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