Citation: Zhao Chen, Xie Han, Jin-Hua Liang, Jun Yin, Guang-Ao Yu, Sheng-Hua Liu. Cycloaddition reactions of benzyne with olefins[J]. Chinese Chemical Letters, ;2014, 25(12): 1535-1539. doi: 10.1016/j.cclet.2014.09.013 shu

Cycloaddition reactions of benzyne with olefins

  • Corresponding author: Guang-Ao Yu,  Sheng-Hua Liu, 
  • Received Date: 4 June 2014
    Available Online: 26 August 2014

    Fund Project: The authors acknowledge financial support from the National Natural Science Foundation of China (Nos. 20931006, 21072070, 21072071, 21272088) (Nos. 20931006, 21072070, 21072071, 21272088)

  • Some novel cycloaddition reactions based on benzyne and olefins have been developed. These reactions were performed in the absence of a transition metal catalyst, and they displayed good yields. These cycloaddition reactions of benzyne with olefins provide effective routes for synthesizing benzocyclobutenes, biaryl compounds and 9,10-dihydrophenanthrene derivatives.
  • 加载中
    1. [1]

      [1] G. Mehta, S. Kotha, Recent chemistry of benzocyclobutenes, Tetrahedron 57 (2001) 625-659.

    2. [2]

      [2] A.K. Sadana, R.K. Saini, W.E. Billups, Cyclobutarenes and related compounds, Chem. Rev. 103 (2003) 1539-1602.

    3. [3]

      [3] W. Oppolzer, Intramolecular cycloaddition reactions of ortho-quinodimethanes in organic synthesis, Synthesis 11 (1978) 793-802.

    4. [4]

      [4] J.L. Charlton, M.M. Alauddin, Orthoquinodimethanes, Tetrahedron 43 (1987) 2873-2889.

    5. [5]

      [5] H. Nemoto, K. Fukumoto, Second generation of steroid synthesis via o-quinodimethane, Tetrahedron 54 (1998) 5425-5464.

    6. [6]

      [6] F.D. Monache, G.D. Monache, J.F. Cavalcanti, et al., An unexpected dihydrophenanthrene from clusia paralycola, Tetrahedron Lett. 28 (1987) 563-566.

    7. [7]

      [7] (a) K. Baba, T. Kido, M. Taniguchi, M. Kozawaqa, Stillbenoids from cassia garrettiana, Phytochemistry 36 (1994) 1509-1513; (b) M.H. Yang, L. Cai, M.H. Li, et al., Three new phenanthrenes from Monomeria barbata Lindl., Chin. Chem. Lett. 21 (2010) 325-328.

    8. [8]

      [8] F. Ullmann, J. Bielecki, Ueber synthesen in der biphenylreihe, Chem. Ber. 34 (1901) 2174-2185.

    9. [9]

      [9] S.P. Stanforth, Catalytic cross-coupling reactions in biaryl synthesis, Tetrahedron 54 (1998) 263-303.

    10. [10]

      [10] J. Hassan, M. Sé vignon, C. Gozzi, E. Schulz, M. Lemaire, Aryl-aryl bond formation one century after the discovery of the Ullmann reaction, Chem. Rev. 102 (2002) 1359-1470.

    11. [11]

      [11] (a) A. Bhunia, S.R. Yetra, A.T. Biju, Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes, Chem. Soc. Rev. 41 (2012) 3140-3152; (b) J. Park, M. Yan, Covalent functionalization of graphene with reactive intermediates, Acc. Chem. Res. 46 (2013) 181-189; (c) A.T. Biju, N. Kuhl, F. Glorius, Extending NHC-catalysis: coupling aldehydes with unconventional reaction partners, Acc. Chem. Res. 44 (2011) 1182-1195; (d) A.M. Dyke, A.J. Hester, G.C. Lloyd-Jones, Organometallic generation and capture of ortho-arynes (Stuttgart), Synthesis 24 (2006) 4093-4112.

    12. [12]

      [12] (a) H. Yoshida, K. Takaki, Multicomponent coupling reaction of arynes for construction of heterocyclic skeletons, Heterocycles 85 (2012) 1333-1349;(b) P.M. Tadross, B.M. Stoltz, A comprehensive history of arynes in natural product total synthesis, Chem. Rev. 112 (2012) 3550-3577; (c) C.M. Gampe, E.M. Carreira, Arynes and cyclohexyne in natural product synthesis, Angew. Chem. Int. Ed. 51 (2012) 3766-3778; (d) L. He, J.X. Pian, J. Zhang, Y.Z. Li, Highly efficient synthesis of 9-aminoxanthenes via the tandem reaction of arynes with salicyl N-tosylimines, Chin. Chem. Lett. 23 (2012) 1359-1362.

    13. [13]

      [13] Y. Himeshima, T. Sonoda, H. Kobayashi, Fluoride-induced 1,2-elimination of otrimethylsilylphenyl triflate to benzyne under mild conditions, Chem. Lett. 12 (1983) 1211-1214.

    14. [14]

      [14] M. Chaumontet, R. Piccardi, N. Audic, et al., Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: method and mechanistic study, J. Am. Chem. Soc. 130 (2008) 15157-15166.

  • 加载中
    1. [1]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    2. [2]

      Ning LISiyu DUXueyi WANGHui YANGTao ZHOUZhimin GUANPeng FEIHongfang MAShang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372

    3. [3]

      Hao-Cong LiMing ZhangQiyan LvKai SunXiao-Lan ChenLingbo QuBing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579

    4. [4]

      Ruowen Liang Chao Zhang Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211

    5. [5]

      Weichen WANGChunhua GONGJunyong ZHANGYanfeng BIHao XUJingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO2 cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415

    6. [6]

      Gangsheng LiXiang YuanFu LiuZhihua LiuXujie WangYuanyuan LiuYanmin ChenTingting WangYanan YangPeicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880

    7. [7]

      . . University Chemistry, 2024, 39(9): 0-0.

    8. [8]

      Xinqiong LiGuocheng RaoXi PengChan YangYanjing ZhangYan TianXianghui FuJia Geng . Direct detection of C9orf72 hexanucleotide repeat expansions by nanopore biosensor. Chinese Chemical Letters, 2024, 35(5): 109419-. doi: 10.1016/j.cclet.2023.109419

    9. [9]

      Yan LiuYang WangJiayi ZhuXuxian SuXudong LinLiang XuXiwen Xing . Employing pH-responsive RNA triplex to control CRISPR/Cas9-mediated gene manipulation in mammalian cells. Chinese Chemical Letters, 2024, 35(9): 109427-. doi: 10.1016/j.cclet.2023.109427

    10. [10]

      Guo-Ping YinYa-Juan LiLi ZhangLing-Gao ZengXue-Mei LiuChang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035

    11. [11]

      Jiajun WangGuolin YiShengling GuoJianing WangShujuan LiKe XuWeiyi WangShulai Lei . Computational design of bimetallic TM2@g-C9N4 electrocatalysts for enhanced CO reduction toward C2 products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050

    12. [12]

      Peng GuoShicheng DongXiang-Gui ZhangBing-Bin YangJun ZhuKe-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052

    13. [13]

      Qiuye WangYabing SunLiangxue LaiHaijing CuiYonglong YeMing YangWeihao ZhuBo YuanQuanliang MaoWenzhi RenAiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212

    14. [14]

      Hao GUOTong WEIQingqing SHENAnqi HONGZeting DENGZheng FANGJichao SHIRenhong LI . Electrocatalytic decoupling of urea solution for hydrogen production by nickel foam-supported Co9S8/Ni3S2 heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2141-2154. doi: 10.11862/CJIC.20240085

    15. [15]

      Yuan TengZichun ZhouJinghua ChenSiying HuangHongyan ChenDaibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs3Bi2Br9/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430

    16. [16]

      Cheng PENGJianwei WEIYating CHENNan HUHui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs3Bi2X9 (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282

    17. [17]

      Ruiheng LiangHuizhong WuZhongzheng HuGe SongXuyang ZhangOmotayo A. ArotibaMinghua Zhou . Hierarchical Fe-Bi/Bi7O9I3/OVs microspheres coupled with natural air diffusion electrode to achieve efficient heterogeneous visible-light-driven photoelectro-Fenton degradation of tetracycline without aeration. Chinese Chemical Letters, 2025, 36(4): 110136-. doi: 10.1016/j.cclet.2024.110136

Metrics
  • PDF Downloads(0)
  • Abstract views(645)
  • HTML views(0)

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