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Ruthenium-Catalyzed Cascade Reactions of Diynes with Norbornadiene – Synthesis of Norbornene Derivatives†‡

  1. Chu-Chun Cheng1,
  2. Chia-Sen Chang1,
  3. Yu-Lin Hsu1,
  4. Ting-Yu Lee2,
  5. Ling-Chueh Chang2,
  6. Shih-Hsien Liu3,
  7. Yao-Ting Wu1

Article first published online: 8 DEC 2009

DOI: 10.1002/ejoc.200901039

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2010, Issue 4, pages 672–679, February 2010

Additional Information

How to Cite

Cheng, C.-C., Chang, C.-S., Hsu, Y.-L., Lee, T.-Y., Chang, L.-C., Liu, S.-H. and Wu, Y.-T. (2010), Ruthenium-Catalyzed Cascade Reactions of Diynes with Norbornadiene – Synthesis of Norbornene Derivatives. European Journal of Organic Chemistry, 2010: 672–679. doi: 10.1002/ejoc.200901039

Author Information

  1. 1

    Department of Chemistry, National Cheng-Kung University, No. 1 Ta-Hsueh Road, 701 Tainan, Taiwan, Fax: +886-6-2740552

  2. 2

    Department of Applied Chemistry, National University of Kaohsiung, No. 700 Kaohsiung University Rd., 811 Kaohsiung, Taiwan

  3. 3

    Material and Chemical Research Laboratories, Industrial Technology Research Institute, 195 Chung Hsing Rd., Sec. 4 Chu Tung, 310 Hsin Chu, Taiwan

  1. †

    Metal-Catalyzed Reactions of Alkynes, IV. Part III: Y.-T. Wu, M.-Y. Kuo, Y.-T. Chang, C.-C. Shin, T.-C. Wu, C.-C. Tai, T.-H. Cheng, W.-S. Liu, Angew. Chem.2008, 120, 10039–10042; Angew. Chem. Int. Ed.2008, 47, 9891–9894. Part II: Y.-T. Wu, W.-C. Lin, C.-J. Liu, C.-Y. Wu, Adv. Synth. Catal.2008, 350, 1841–1849.

  2. ‡

    Dedicated to Professor Pei-Lin Wu on the occasion of her 60th birthday

Publication History

  1. Issue published online: 18 JAN 2010
  2. Article first published online: 8 DEC 2009
  3. Manuscript Received: 10 SEP 2009

Funded by

  • National Science Council of Taiwan. Grant Number: NSC96-2113-M-006-008-MY2

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Keywords:

  • Norbornadiene;
  • Norbornene;
  • Cascade reaction;
  • Ruthenium;
  • Transfer hydrogenation;
  • Cycloaddition

Graphical Abstract

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Norbornene derivatives were prepared from norbornadiene and diynes under the catalysis of Ru complexes. This cascade reaction provided high diastereoselectivity.Additionally, one of these cycloadducts was applied in the synthesis of polynorbornenes by the ring-opening metathesis polymerization.

Abstract

Norbornene derivatives 7–11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7–11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7-diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbornene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (Mn) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.

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