Citation: Wu Zhengxing, Zhang Wanbin. Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2250-2262. doi: 10.6023/cjoc201704031 shu

Recent Advances in Metal-Catalyzed 1, 2-Difunctionalization of Conjugated Dienes

  • Corresponding author: Zhang Wanbin, wanbin@sjtu.edu.cn
  • Received Date: 18 April 2017
    Revised Date: 22 May 2017
    Available Online: 24 September 2017

    Fund Project: the Program of Shanghai Subject Chief Scientists 14XD1402300the National Natural Science Foundation of China 21232004the National Natural Science Foundation of China 21672142the Basic Research Foundation of Shanghai Science and Technology Committee 15JC1402200Project supported by the National Natural Science Foundation of China (Nos. 21232004, 21672142), the Program of Shanghai Subject Chief Scientists (No.14XD1402300) and the Basic Research Foundation of Shanghai Science and Technology Committee (No. 15JC1402200)

Figures(9)

  • The 1, 2-difunctionalization of conjugated dienes is an important homogeneous catalytic reaction. The obtained products through 1, 2-difunctionalization are widely existed in natural products and bioactive compounds, and are also sources of important organic intermediates, in addition, the preserved double bond in the difunctionalized product can be further transformed to give the desired structures or be functionalized sequentially to achieve multi-functionalization. The main difficulties focus on the encountered complex selectivities, including the regioselectivity, chemoselectivity and stereoselectivity in reactions. In recent years, with the development of organometallic chemistry, metal palladium, copper, iron or silver catalyzed 1, 2-difunctionalizations of conjugated dienes have been reported in succession. In some cases the enantioselective 1, 2-difunctionalizations of conjugated dienes were achieved via the introduction of chiral ligands. This review mainly focus on the recent metal catalyzed 1, 2-difunctionalizations of conjugated dienes.
  • 加载中
    1. [1]

    2. [2]

    3. [3]

      Prileschajew, N. Eur. J. Inorg. Chem. 1909, 42, 4811.

    4. [4]

      Gilman, H. Organic Chemistry:An Advanced Treatise, Vol. 1, Wiley, New York, 1938, p. 36.

    5. [5]

      (a) Criegee, R. Justus Liebigs Ann. Chem. 1936, 522, 75.
      (b) Criegee, R. Angew. Chem. 1937, 50, 153.

    6. [6]

      Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1967, 89, 1950.  doi: 10.1021/ja00984a034

    7. [7]

      (a) Sharpless, K. B.; Patrick, D. W.; Truesdale, L. K.; Biller, S. A. J. Am. Chem. Soc. 1975, 97, 2305.
      (b) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420.

    8. [8]

      (a) Bäckvall, J.-E. Tetrahedron Lett. 1978, 19, 163.
      (b) Bäckvall, J.-E.; Björkman, E. E. J. Org. Chem. 1980, 45, 2893.

    9. [9]

      (a) Sharpless, K. B.; Chong, A. O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
      (b) Hentges, S. G.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 4263.
      (c) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
      (d) Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.

    10. [10]

      (a) Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 2523.
      (b) Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
      (c) Palmgren, A.; Larsson, A. L. E.; Bäckvall, J.-E. J. Org. Chem. 1999, 64, 836.
      (d) Löfstedt, J.; Närhi, K.; Dorange, I.; Bäckvall, J.-E. J. Org. Chem. 2003, 68, 7243.
      (e) Verboom, R. C.; Persson, B. A.; Bäckvall, J.-E. J. Org. Chem. 2004, 69, 3102.
      (f) Piera, J.; Persson, A.; Caldentey, X.; Bäckvall, J.-E. J. Am. Chem. Soc. 2007, 129, 14120.
      (g) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 9134.
      (h) Schuster, C. H.; Li, B.; Morken, J. P. Angew. Chem. Int. Ed. 2011, 50, 7906.

    11. [11]

      Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7571.  doi: 10.1021/ja00045a044

    12. [12]

      O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.  doi: 10.1021/jo00154a010

    13. [13]

      (a) Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
      (b) Larock, R. C.; Berrios-Pena, N. G.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.

    14. [14]

      (a) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
      (b) Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523.

    15. [15]

      Liao, L.; Jana, R.; Urkalan, K. B.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 5784.  doi: 10.1021/ja201358b

    16. [16]

      Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662.  doi: 10.1021/jo00193a047

    17. [17]

      Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.  doi: 10.1021/ja051181d

    18. [18]

      Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066.  doi: 10.1021/ja803397y

    19. [19]

      Xing, D.; Yang, D. Org. Lett. 2013, 15, 4370.  doi: 10.1021/ol401901h

    20. [20]

      Cooper, S. P.; Booker-Milburn, K. I. Angew. Chem. Int. Ed. 2015, 54, 6496.  doi: 10.1002/anie.201501037

    21. [21]

      (a) Kagechika, K.; Shibasaki, M. J. Org. Chem. 1991, 56, 4093.
      (b) Kagechika, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 1993, 49, 1773.
      (c) Ohshima, T.; Kagechika, K.; Adachi, A.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108.

    22. [22]

      Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 11688.  doi: 10.1021/ja074698t

    23. [23]

      Cornwall, R. G.; Zhao, B.; Shi, Y. Org. Lett. 2013, 15, 796.  doi: 10.1021/ol303469a

    24. [24]

      Stokes, B. J.; Liao, L.; de Andrade, A. M.; Wang, Q.; Sigman, M. S. Org. Lett. 2014, 16, 4666.  doi: 10.1021/ol502279u

    25. [25]

      Wu, X.; Lin, H.-C.; Li, M.-L.; Li, L. L.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 13476.  doi: 10.1021/jacs.5b08734

    26. [26]

      Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314.  doi: 10.1021/jacs.6b00976

    27. [27]

      Chen, S.-S.; Meng, J.; Li, Y.-H.; Han, Z.-Y. J. Org. Chem., 2016, 81, 9402.  doi: 10.1021/acs.joc.6b01611

    28. [28]

      Chen, S.-S.; Wu, M.-S.; Han, Z.-Y. Angew. Chem., Int. Ed. 2017, 56, 6641.  doi: 10.1002/anie.201702745

    29. [29]

      Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589.  doi: 10.1021/ol071105a

    30. [30]

      Zhao, B.; Peng, X.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 11009.  doi: 10.1021/ja103838d

    31. [31]

      Zhao, B.; Peng, X.; Zhu, Y.; Ramirez, T. A.; Cornwall, R. G.; Shi, Y. J. Am. Chem. Soc. 2011, 133, 20890.  doi: 10.1021/ja207691a

    32. [32]

      Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 6610.  doi: 10.1021/ja800495r

    33. [33]

      Du, H.; Zhao, B.; Yuan, W.; Shi, Y. Org. Lett. 2008, 10, 4231.  doi: 10.1021/ol801605w

    34. [34]

      Zhao, B.; Du, H.; Shi, Y. J. Org. Chem. 2009, 74, 8392.  doi: 10.1021/jo901685c

    35. [35]

      Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570.  doi: 10.1021/ja1013536

    36. [36]

      Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370.  doi: 10.1021/ja3046684

    37. [37]

      (a) Llaveria, J.; Beltrán, Á.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Pérez, P. J. Angew. Chem. Int. Ed. 2010, 49, 7092.
      (b) Llaveria, J.; Beltrán, Á.; Sameera, W. M. C.; Locati, A.; Díaz-Requejo, M. M.; Matheu, M. I.; Castillón, S.; Maseras, F.; Pérez, P. J. J. Am. Chem. Soc. 2014, 136, 5342.

  • 加载中
    1. [1]

      Yajun Hou ,  Jinxin Liu ,  Tao Chen ,  Yi Zhang ,  Lei Zhou . Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum. University Chemistry, 2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101

    2. [2]

      Yuanyuan Ping ,  Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092

    3. [3]

      Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195

    4. [4]

      Danqing Wu ,  Jiajun Liu ,  Tianyu Li ,  Dazhen Xu ,  Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

    5. [5]

      Junyuan Zhang ,  Xiangzheng Ren ,  Zhiwei Miao . 烯烃1,3-双官能团化反应研究进展. University Chemistry, 2026, 41(8): 148-161. doi: 10.12461/PKU.DXHX202507121

    6. [6]

      Mengfan Gong ,  Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036

    7. [7]

      Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201

    8. [8]

      Xiaomin Kang ,  Chuanbao Jiao . Application of Metal-Organic Frameworks in CO2 Catalytic Conversion: Promoting “Double Carbon” Actions for a Beautiful China. University Chemistry, 2026, 41(2): 208-217. doi: 10.12461/PKU.DXHX202503011

    9. [9]

      Haiyan Fu ,  Chunchun Zhang ,  Xueli Zheng ,  Taotao Hao ,  Weichao Xue ,  Jiaqi Xu ,  Shunxi Dong ,  Ruixiang Li ,  Hua Chen . “金属有机化学与催化”课程项目化教学改革探索与实践. University Chemistry, 2026, 41(10): 65-72. doi: 10.12461/PKU.DXHX202510067

    10. [10]

      Zhuoming Liang ,  Ming Chen ,  Zhiwen Zheng ,  Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

    11. [11]

      Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO2 Methanation of Derived Ni-Al2O3 Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002

    12. [12]

      Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO2 Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026

    13. [13]

      Guoqiang Peng , Xiuyan Li , Min Li , Zhibo Su , Falu Hu , Guowei Zhou . Engineering efficient metal-organic frameworks for photocatalytic CO2 reduction. Acta Physico-Chimica Sinica, 2026, 42(2): 100164-0. doi: 10.1016/j.actphy.2025.100164

    14. [14]

      Hongjing ZHU , Guanying LIU , Kuaibing WANG . Application of in-situ characterization in electrocatalytic CO2 reduction reaction of metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(9): 1893-1909. doi: 10.11862/CJIC.20260144

    15. [15]

      Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409

    16. [16]

      Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291

    17. [17]

      Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031

    18. [18]

      Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067

    19. [19]

      Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO2 adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220

    20. [20]

      Yingying Yu ,  Hang Xu . 基于X-射线单晶衍射精准构筑簇基金属有机框架及其CO2催化转化. University Chemistry, 2026, 41(10): 132-142. doi: 10.12461/PKU.DXHX202511033

Metrics
  • PDF Downloads(86)
  • Abstract views(5092)
  • HTML views(1000)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return