Citation: Kunbing Ouyang, Zhenfeng Xi. Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes[J]. Chinese Journal of Catalysis, ;2015, 36(1): 24-32. doi: 10.1016/S1872-2067(14)60201-1 shu

Pd-catalyzed cyclodimerization of alkenyl and aryl dibromides: Construction of dibenzo[a,e]cyclooctatetraenes

  • Corresponding author: Zhenfeng Xi, 
  • Received Date: 30 June 2014
    Available Online: 21 July 2014

    Fund Project: 国家重点基础研究发展计划(973计划, 2012CB821600) (973计划, 2012CB821600) 国家自然科学基金(21132001). (21132001)

  • Cyclooctatetraenes, including dibenzocyclooctatetraenes, are structurally interesting compounds and are widely used in many areas. Therefore, the development of synthetic methods for such compounds has long been attractive. In this work, a Pd-catalyzed coupling reaction between alkenylbromides and arylbromides has been realized. Multi-substituted 1,4-dibromo-1,3-butadienes and o-bromo-2-(2-bromovinyl)benzenes underwent a Pd-catalyzed cyclodimerization reaction to afford the corresponding multi-substituted cyclooctatetraenes and dibenzo[a,e] cyclooctatetraenes, respectively, in high yields and with excellent regioselectivity.
  • 加载中
    1. [1]

      [1] Huisgen R, Mietzsch F. Angew Chem Int Ed, 1964, 3: 83

    2. [2]

      [2] Paquette L A. Tetrahedron, 1975, 31: 2855

    3. [3]

      [3] Schumann H. Angew Chem Int Ed, 1984, 23: 474

    4. [4]

      [4] Paquette L A. Acc Chem Res, 1993, 26: 57

    5. [5]

      [5] Klärner F G. Angew Chem Int Ed, 2001, 40: 3977

    6. [6]

      [6] Nishinaga T, Ohmae T, Iyoda M. Symmetry, 2010, 2: 76

    7. [7]

      [7] Edelmann F T. Angew Chem Int Ed, 1995, 34: 2466

    8. [8]

      [8] Edelmann F T. New J Chem, 1995, 19: 535

    9. [9]

      [9] Edelmann F T. In: Abel E W, Stone F G A, Wilkinson G eds. Comprehensive Organometallic Chemistry II. Pergamon Press, Oxford, 1995

    10. [10]

      [10] Schumann H, Meese-Marktscheffel J A, Esser L. Chem Rev, 1995, 95: 865

    11. [11]

      [11] Wang C, Xi Z F. Chem Commun, 2007: 5119

    12. [12]

      [12] Komatsu K. Bull Chem Soc Jpn, 2001, 74: 407

    13. [13]

      [13] Hui C W, Mak T C W, Wong H N C. Tetrahedron, 2004, 60: 3523

    14. [14]

      [14] Lai C W, Lam C K, Lee H K, Mak T C W, Wong H N C. Org Lett, 2003, 5: 823

    15. [15]

      [15] Lawrie C J, Gable K P, Carpenter B K. Organometallics, 1989, 8: 2274

    16. [16]

      [16] Esser B, Bandyopadhyay A, Rominger F, Gleiter R. Chem Eur J, 2009, 15: 3368

    17. [17]

      [17] Carnes M, Buccella D, Decatur J, Steigerwald M L, Nuckolls C. Angew Chem Int Ed, 2008, 47: 2982

    18. [18]

      [18] Takahashi T, Sun W H, Nakajima K. Chem Commun, 1999: 1595

    19. [19]

      [19] Li G T, Fang H Y, Zhang S W, Xi Z F. Tetrahedron Lett, 2004, 45: 8399

    20. [20]

      [20] Wang C, Yuan J, Li G T, Wang Z T, Zhang S W, Xi Z F. J Am Chem Soc, 2006, 128: 4564

    21. [21]

      [21] Wei J N, Wang Z T, Zhang W X, Xi Z F. Org Lett, 2013, 15: 1222

    22. [22]

      [22] Geng W Z, Wei J N, Zhang W X, Xi Z F. J Am Chem Soc, 2014, 136: 610

    23. [23]

      [23] Yamamoto Y, Ohno T, Itoh K. Chem Commun, 1999: 1543

    24. [24]

      [24] Yamamoto Y, Ohno T, Itoh K. Chem Eur J, 2002, 8: 4734

    25. [25]

      [25] Chen C, Xi C J, Lai C B, Wang R J, Hong X Y. Eur J Org Chem, 2004: 647

    26. [26]

      [26] Wender P A, Christy J P. J Am Chem Soc, 2007, 129: 13402

    27. [27]

      [27] Wender P A, Christy J P, Lesser A B, Gieseler M T. Angew Chem Int Ed, 2009, 48: 7687

    28. [28]

      [28] Ubayama H, Sun W H, Takahashi T, Xi Z F. Chem Commun, 1998: 1931

    29. [29]

      [29] Eisch J J, Piotrowski A M, Han K I, Krüger C, Tsay Y H. Organometallics, 1985, 4: 224

    30. [30]

      [30] Edelbach B L, Lachicotte R J, Jones W D. J Am Chem Soc, 1998, 120: 2843

    31. [31]

      [31] Perthuisot C, Edelbach B L, Zubris D L, Simhai N, Iverson C N, Müller C, Satoh T, Jones W D. J Mol Catal A, 2002, 189: 157

    32. [32]

      [32] Masselot D, Charmant J P H, Gallagher T. J Am Chem Soc, 2006, 128: 694

    33. [33]

      [33] Schaub T, Backes M, Radius U. Organometallics, 2006, 25: 4196

    34. [34]

      [34] Ananikov V P, Hazipov O V, Beletskaya I P. Chem Asian J, 2011, 6: 306

    35. [35]

      [35] Negishi E, Cederbaum F E, Takahashi T. Tetrahedron Lett, 1986, 27: 2829

    36. [36]

      [36] Yasuike S, Ohta H, Shiratori S, Kurita J, Tsuchiya T. J Chem Soc, Chem Commun, 1993: 1817

    37. [37]

      [37] Teplý F, Stará I G, Starý I, Kollárovič A, Šaman D, Rulíšek L, Fiedler P. J Am Chem Soc, 2002, 124: 9175

    38. [38]

      [38] Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F. Angew Chem Int Ed, 2006, 45: 6893

    39. [39]

      [39] Ball C J, Gilmore J, Willis M C. Angew Chem Int Ed, 2012, 51: 5718

    40. [40]

      [40] Muzalevskiy V M, Nenajdenko V G, Shastin A V, Balenkova E S, Haufe G. Synthesis, 2009: 2249

    41. [41]

      [41] Corey J C, John C S, Ohmsted M C, Chang L S. J Organomet Chem, 1986, 304: 93

    42. [42]

      [42] Liu Y X, Stringfellow T C, Ballweg D, Guzei I A, West R. J Am Chem Soc, 2002, 124: 49

    43. [43]

      [43] Chang L S, Corey J Y. Organometallics, 1989, 8: 1885

    44. [44]

      [44] Shimizu M, Tomioka Y, Nagao I, Kadowaki T, Hiyama T. Chem Asian J, 2012, 7: 1644

    45. [45]

      [45] Willis M C, Brace G N, Findlay T J K, Holmes I P. Adv Synth Catal, 2006, 348: 851

    46. [46]

      [46] Shen Q L, Hartwig J F. J Am Chem Soc, 2006, 128: 10028

    47. [47]

      [47] Liang Y, Meng T H, Zhang H J, Xi, Z F. Synlett, 2011: 911

    48. [48]

      [48] Tadd A C, Matsuno A, Fielding M R, Willis M C. Org Lett, 2009, 11: 583

    49. [49]

      [49] Kundu D, Maity P, Ranu B C. Org Lett, 2014, 16: 1040

    50. [50]

      [50] Geng W Z, Zhang W X, Hao W, Xi Z F. J Am Chem Soc, 2012, 134: 20230

    51. [51]

      [51] Fang H Y, Li G T, Mao G L, Xi Z F. Chem Eur J, 2004, 10: 3444

    52. [52]

      [52] Liang Y, Geng W Z, Wei J N, Ouyang K B, Xi Z F. Org Biomol Chem, 2012, 10: 1537

    53. [53]

      [53] Xi Z F. Acc Chem Res, 2010, 43: 1342

    54. [54]

      [54] Wei J N, Liu L, Zhan M, Xu L, Zhang W X, Xi Z F. Angew Chem Int Ed, 2014, 53: 5634

    55. [55]

      [55] Li H, Wei B S, Xu L, Zhang W X, Xi Z F. Angew Chem Int Ed, 2013, 52: 10822

    56. [56]

      [56] Zhou Y, Zhang W X, Xi Z F. Organometallics, 2012, 31: 5546

    57. [57]

      [57] Zhang H J, Wei J N, Zhao F, Liang Y, Wang Z T, Xi Z F. Chem Commun, 2010, 46: 7439

    58. [58]

      [58] Schaub T, Radius U. Chem Eur J, 2005, 11: 5024

    59. [59]

      [59] Sheldrick G M. SHELXTL 5.10 for Windows NT: Structure Determination Software Programs. Bruker Analytical X-ray Systems, Inc., Madison, WI, 1997

    60. [60]

      [60] Sheldrick G M. Acta Cryst A, 2008, 64: 112

    61. [61]

      [61] Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K, Puschmann H. J Appl Cryst, 2009, 42: 339

    62. [62]

      [62] Ouyang K B, Xi Z F. Acta Chim Sin, 2013, 71: 13

    63. [63]

      [63] Hassan J, Hathroubi C, Gozzi C, Lemaire M. Tetrahedron, 2001, 57: 7845

    64. [64]

      [64] Hassan J, Penalva V, Lavenot L, Gozzi C, Lemaire M. Tetrahedron, 1998, 54: 13793

    65. [65]

      [65] Shao L J, Du Y J, Zeng M F, Li X D, Shen W T, Zuo S F, Lu Y Q, Zhang X M, Qi C Z. Appl Organometal Chem, 2010, 24: 421

    66. [66]

      [66] Nadri S, Azadi E, Ataei A, Joshaghani M, Rafiee E. J Organomet Chem, 2011, 696: 2966

    67. [67]

      [67] Sehnal P, Taylor R J K, Fairlamb I J S. Chem Rev, 2010, 110: 824

    68. [68]

      [68] Xu L M, Li B J, Yang Z, Shi Z J. Chem Soc Rev, 2010, 39: 712

    69. [69]

      [69] Mu X, Wu T, Wang H Y, Guo Y L, Liu G S. J Am Chem Soc, 2012, 134: 878

    70. [70]

      [70] Canty A J, Patel J, Rodemann T, Ryan J H, Skelton B W, White A H. Organometallics, 2004, 23: 3466

  • 加载中
    1. [1]

      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

    2. [2]

      Yinwu Su Xuanwen Zheng Jianghui Du Boda Li Tao Wang Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092

    3. [3]

      Chi Li Jichao Wan Qiyu Long Hui Lv Ying XiongN-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016

    4. [4]

      Juntao Yan Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024

    5. [5]

      Yanhui Zhong Ran Wang Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017

    6. [6]

      Yihao Zhao Jitian Rao Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

    7. [7]

      Jiahui YUJixian DONGYutong ZHAOFuping ZHAOBo GEXipeng PUDafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO4:Yb3+,Er3+ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1

    8. [8]

      Xiao SANGQi LIUJianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158

    9. [9]

      Zhiquan Zhang Baker Rhimi Zheyang Liu Min Zhou Guowei Deng Wei Wei Liang Mao Huaming Li Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029

    10. [10]

      Bing WEIJianfan ZHANGZhe 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

    11. [11]

      Xiuyun Wang Jiashuo Cheng Yiming Wang Haoyu Wu Yan Su Yuzhuo Gao Xiaoyu Liu Mingyu Zhao Chunyan Wang Miao Cui Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067

    12. [12]

      Rui Gao Ying Zhou Yifan Hu Siyuan Chen Shouhong Xu Qianfu Luo Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050

    13. [13]

      Renxiao Liang Zhe Zhong Zhangling Jin Lijuan Shi Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

    14. [14]

      Geyang Song Dong Xue Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030

    15. [15]

      Ruolin CHENGHaoran WANGJing RENYingying MAHuagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349

    16. [16]

      Yanan Liu Yufei He Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081

    17. [17]

      Caixia Lin Zhaojiang Shi Yi Yu Jianfeng Yan Keyin Ye Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

    18. [18]

      Yanglin Jiang Mingqing Chen Min Liang Yige Yao Yan Zhang Peng Wang Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027

    19. [19]

      Lina Guo Ruizhe Li Chuang Sun Xiaoli Luo Yiqiu Shi Hong Yuan Shuxin Ouyang Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

    20. [20]

      Feng Han Fuxian Wan Ying Li Congcong Zhang Yuanhong Zhang Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181

Metrics
  • PDF Downloads(163)
  • Abstract views(497)
  • HTML views(10)

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