Modular Synthesis of Arylalkanes Using Organosulfur Compounds

• Project/Area Number: 26810056
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University
• Principal Investigator: Nambo Masakazu 名古屋大学, トランスフォーマティブ生命分子研究所, 特任助教 (10705528)
• Research Collaborator: CRUDDEN Cathleen M. クイーンズ大学, 教授
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: アリールアルカン / 炭素-スルホニル結合活性化 / 有機硫黄化合物 / パラジウム触媒 / 逐次的自在合成 / C-H官能基化 / 有機ホウ素化合物 / アゾール / アリール化 / スルホン / スカンジウム触媒 / トリアリールメタン

Outline of Final Research Achievements

We have developed methyl sulfone derivatives as new reacting templates in Pd-catalyzed sequential arylations directed toward the modular synthesis of multiply-arylated methanes. This method enabled the rapid synthesis of thyroid hormone receptor b-selective analog (GC-24) and the development of new inhibitor for plant cell division.

Research Products

• [Int'l Joint Research] クイーンズ大学(カナダ)
• [Int'l Joint Research]
• [Int'l Joint Research] クイーンズ大学(カナダ)
• [Int'l Joint Research]
• [Journal Article] 1. Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions (2017)
  • Author(s): Masakazu Nambo, Eric C. Keske, Jason P. G. Rygus, Jacky, C.-H. Yim, Cathleen M. Crudden
  • Journal Title: ACS Catalysis Volume: 7 Issue: 2 Pages: 1108-1112
  • DOI: 10.1021/acscatal.6b03434
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Combination of synthetic chemistry and live-cell imaging identified a rapid cell division inhibitor in tobacco and Arabidopsis thaliana (2016)
  • Author(s): Nambo, M., Kurihara, D., Yamada, T., Nishiwaki-Ohkawa, T., Kadofusa, N., Kimata, Y., Kuwata, K., Umeda, M. and Ueda, M.
  • Journal Title: Plant Cell Physiol. Volume: 57 Issue: 11 Pages: 2255-2268
  • DOI: 10.1093/pcp/pcw140
  • NAID: 120006220249
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] 4. Arylative Desulfonation of Diarylmethyl Phenyl Sulfones with Arenes Catalyzed by Scandium Triflate (2016)
  • Author(s): Masakazu Nambo, Zachary T. Ariki, Daniel Canseco-Gonzalez, D. Dawson Beattie, Cathleen M. Crudden
  • Journal Title: Organic Letters Volume: 18 Issue: 10 Pages: 2339-2342
  • DOI: 10.1021/acs.orglett.6b00744
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Iterative protecting group-free cross-coupling leading to chiral multiply arylated structures (2016)
  • Author(s): Cathleen M. Crudden, Christopher Ziebenhaus, Jason P. G. Rygus, Kazem Ghozati, Phillip J. Unsworth,Masakazu Nambo, Samantha Both, Marieke Hutchinson, Veronique S. Laberge, Yuuki Maekawa, Daisuke Imao
  • Journal Title: Nature communication Volume: 7 Issue: 1 Pages: 1-7
  • DOI: 10.1038/ncomms11065
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Recent Advances in the Synthesis of Triarylmethanes by Transition Metal Catalysis (2015)
  • Author(s): Masakazu Nambo, Cathleen M. Crudden
  • Journal Title: ACS catalysis Volume: 5 Issue: 8 Pages: 4734-4742
  • DOI: 10.1021/acscatal.5b00909
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri-and Tetraarylmethanes (2015)
  • Author(s): M. Nambo, M. Yar, J.D. Smith, C.M. Crudden
  • Journal Title: Organic Letters Volume: 17 Issue: 1 Pages: 50-53
  • DOI: 10.1021/ol503213z
  • Peer Reviewed
• [Presentation] Water-soluble N-heterocyclic carbene protected gold nanoparticles for biological applications (2017)
  • Author(s): Kirsi Salorinne, Renee Man, Henry Li, Masayasu Taki, Masakazu Nambo, Cathleen M. Crudden
  • Organizer: 第97春季年会
  • Place of Presentation: 慶応大学
• [Presentation] Enhanced stability: Synthesis and characterizations of N-heterocyclic carbene-stabilized gold nanoparticles (2017)
  • Author(s): Renee Man, Henry Li, Masakazu Nambo, Cathleen M. Crudden
  • Organizer: 第97春季年会
  • Place of Presentation: 慶応大学
• [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes (2016)
  • Author(s): Masakazu Nambo, Eric, C. Keske, Jason, P. G. Ryugus, Jacky C.-H. Yim, Cathleen M. Crudden
  • Organizer: Gordon Research Conference, Stereochemistry
  • Place of Presentation: Salve Regina University, U.S.
  • Year and Date: 2016-07-27
  • Int'l Joint Research
• [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes (2016)
  • Author(s): Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden
  • Organizer: 第96春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-25
• [Presentation] Pd-catalyzed Desulfonative Cross-Coupling of Diarylmethyl Sulfones with Oxazoles (2016)
  • Author(s): Jacky C.-H. Yim, Masakazu Nambo, Cathleen M. Crudden
  • Organizer: 第96春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-25
• [Presentation] Discovery of New Molecules that Control Cell Division and Cell Cycle (2016)
  • Author(s): Masakazu Nambo, Taeko Nishiwaki-Ohkawa, Minako Ueda, Keiko Kuwata, Daisuke Kurihara, Takashi Yoshimura, Tetsuya Higashiyama, Cathleen Crudden
  • Organizer: 2ND CSRS-ITbM Joint Workshop
  • Place of Presentation: 理研（和光キャンパス）
  • Year and Date: 2016-01-07
• [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes (2016)
  • Author(s): Masakazu Nambo, Jacky C.-H. Yim, Cathleen M. Crudden
  • Organizer: 第63回有機金属化学討論会
  • Place of Presentation: 早稲田大学
• [Presentation] The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation (2015)
  • Author(s): Masakazu Nambo, Muhammad Yar, Joel D. Smith, Cathleen M. Crudden
  • Organizer: 第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Scandium Triflate-Catalyzed Arylative Desulfonation of Diarylmethyl Phenyl Sulfones (2015)
  • Author(s): Zachary, T. Ariki, Masakazu Nambo, Daniel Canseco-Gonzalez, Dawson Beattie, Cathleen M. Crudden
  • Organizer: 第95春季年会
  • Place of Presentation: 日本大学
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone (2014)
  • Author(s): 南保正和, Cathleen M. Crudden
  • Organizer: 第61回有機金属化学討論会
  • Place of Presentation: 九州大学
  • Year and Date: 2014-09-23 – 2014-09-25
• [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone (2014)
  • Author(s): Masakazu Nambo, Cathleen M. Crudden
  • Organizer: IGER International Symposium on Chemical Science in Asia
  • Place of Presentation: 名古屋大学
  • Year and Date: 2014-05-26
• [Presentation] Modular Synthesis of Triarylmethanes through Pd-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone (2014)
  • Author(s): Masakazu Nambo, Cathleen M. Crudden
  • Organizer: The 2nd International Symposium on Transformative Bio-Molecules
  • Place of Presentation: 名古屋大学
  • Year and Date: 2014-05-12
• [Remarks] 植物の細胞分裂を急速に止める新規化合物の発見
  • URL: http://www.itbm.nagoya-u.ac.jp/ja/research/2016/11/PCP-Cell-Cycle.php
• [Remarks] THREE RINGS STOP CELL DIVISION IN PLANTS
  • URL: http://www.globalplantcouncil.org/news-and-events/latest-news/three-rings-stop-cell-division-in-plants-development-of-a-triarylmethane-compound-for-possible-control-of-plant-growth
• [Remarks] 植物の細胞分裂を急速に止める新規化合物の発見
  • URL: https://research-er.jp/articles/view/52160
• [Remarks] Triarylmethane for control of plant growth
  • URL: https://phys.org/news/2016-11-triarylmethane-compound-growth.html
• [Remarks] Three rings stop cell division in plants
  • URL: https://www.sciencedaily.com/releases/2016/11/161125084223.htm
• [Patent(Industrial Property Rights)] 植物細胞分裂抑制剤 (2016)
  • Inventor(s): 植田美那子、南保正和、栗原大輔、桑田啓子、大川妙子
  • Industrial Property Rights Holder: 植田美那子、南保正和、栗原大輔、桑田啓子、大川妙子
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2016-028537
  • Filing Date: 2016-02-18
• [Patent(Industrial Property Rights)] トリ(ヘテロ)アリールアセトニトリルの製造方法 (2015)
  • Inventor(s): 南保、Yar、Crudden
  • Industrial Property Rights Holder: 南保、Yar、Crudden
  • Industrial Property Rights Type: 特許
  • Filing Date: 2015-12-04
  • Overseas
• [Patent(Industrial Property Rights)] トリアリールメタン化合物の製造方法 (2014)
  • Inventor(s): 南保正和, Cathleen Crudden
  • Industrial Property Rights Holder: 南保正和, Cathleen Crudden
  • Industrial Property Rights Type: 特許
  • Filing Date: 2014-10-28
• [Patent(Industrial Property Rights)] トリ（ヘテロ）アリールアセトニトリル化合物の製造方法 (2014)
  • Inventor(s): 南保, Yar, Crudden
  • Industrial Property Rights Holder: 南保, Yar, Crudden
  • Industrial Property Rights Type: 特許
  • Filing Date: 2014-12-12