Citation: Tenglong Guo, Quanbin Jiang, Likun Yu, Zhengkun Yu. Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction[J]. Chinese Journal of Catalysis, ;2015, 36(1): 78-85. doi: 10.1016/S1872-2067(14)60247-3 shu

Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction

  • Corresponding author: Zhengkun Yu, 
  • Received Date: 22 August 2014
    Available Online: 22 September 2014

    Fund Project: 国家自然科学基金(21272232). (21272232)

  • A new method has been developed for the cross-coupling of aryl halides with β-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives.
  • 加载中
    1. [1]

      [1] Nowakowska Z. Eur J Med Chem, 2007, 42: 125

    2. [2]

      [2] Bandgar B P, Gawande S S, Bodade R G, Totre J V, Khobragade C N. Bioorg Med Chem, 2010, 18: 1364

    3. [3]

      [3] Sahu N K, Balbhadra S S, Choudhary J, Kohli D V. Curr Med Chem, 2012, 19: 209

    4. [4]

      [4] Ma S J, Wu L L, Liu M, Wang Y M. Org Biomol Chem, 2012, 10: 3721

    5. [5]

      [5] Patti A, Pedotti S, Grassi T, Idolo A, Guido M, De Donno A. J Organomet Chem, 2012, 716: 216.

    6. [6]

      [6] Ye Y, Wang H, Fan R H. Org Lett, 2010, 12: 2802

    7. [7]

      [7] Ribierre J C, Cheval G, Huber F, Mager L, Fort A, Muller R, Mery S, Nicoud J F. J Appl Phys, 2002, 91: 1710

    8. [8]

      [8] Ravindra H J, Kiran A J, Nooji S R. Dharmaprakash S M, Chandrasekharan K, Kalluraya B, Rotermund F. J Cryst Growth, 2008, 310: 2543

    9. [9]

      [9] Liu M, Wilairat P, Go M L. J Med Chem, 2001, 44: 4443

    10. [10]

      [10] Wu X F, Neumann H, Spannenberg A, Schulz T, Jiao H J, Beller M. J Am Chem Soc, 2010, 132: 14596

    11. [11]

      [11] Pennell M N, Unthank M G., Turner P, Sheppard T D. J Org Chem, 2011, 76: 1479

    12. [12]

      [12] Wang J, Liu C, Yuan J W, Lei A W. Angew Chem Int Ed, 2013, 52: 2256

    13. [13]

      [13] Yu S J, Li X W. Org Lett, 2014, 16: 1220

    14. [14]

      [14] Heck R F. Acc Chem Res, 1979, 12: 146

    15. [15]

      [15] Bianco A, Cavarischia C, Farina A, Marcella G, Carolina M. Tetrahedron Lett, 2003, 44: 9107

    16. [16]

      [16] Bianco A, Cavarischia C, Guiso M. Eur J Org Chem, 2004: 2894

    17. [17]

      [17] Yu J Q, Wu H C, Corey E J. Org Lett, 2005, 7: 1415.

    18. [18]

      [18] Uyanik M, Akakura M, Ishihara K. J Am Chem Soc, 2009, 131: 251

    19. [19]

      [19] Zhou J, Wu G, Zhang M, Jie X M, Su W P. Chem Eur J, 2012, 18: 8032

    20. [20]

      [20] Shang Y P, Jie X M, Zhou J, Hu P, Huang S J, Su W P. Angew Chem Int Ed, 2013, 52: 1299

    21. [21]

      [21] Unoh Y, Hirano K, Satoh T, Miura M. J Org Chem, 2013, 78: 5096

    22. [22]

      [22] Jiang Q B, Guo T L, Wang Q F, Wu P, Yu Z K. Adv Synth Catal, 2013, 355: 1874

    23. [23]

      [23] Guo T L, Jiang Q B, Huang F, Chen J P, Yu Z K. Org Chem Front, 2014, 1: 707

    24. [24]

      [24] Tietze L F. Chem Rev, 1996, 96: 115

    25. [25]

      [25] Ding B Q, Zhang Z F, Liu Y G, Sugiya M, Imamoto T, Zhang W B. Org Lett, 2013, 15: 3690

    26. [26]

      [26] Rajput J K, Kaur G. Tetrahedron Lett, 2012, 53: 646

    27. [27]

      [27] Batovska D, Parushev St, Slavova A, Bankova V, Tsvetkova I, Ninova M, Najdenski H. Eur J Med Chem, 2007, 42: 87

    28. [28]

      [28] Ranu B C, Jana R. J Org Chem, 2005, 70: 8621

    29. [29]

      [29] Lü P C, Sun J A, Luo Y, Yang Y, Zhu H L. Bioorg Med Chem Lett, 2010, 20: 4657

    30. [30]

      [30] Weber W M, Decka L M, Vander Jagtb D L. Bioorg Med Chem, 2006, 14: 2450

    31. [31]

      [31] Solomek T, Stacko P, Veetil A T, Pospisil T, Klan P. J Org Chem, 2010, 75: 7300

    32. [32]

      [32] Tsukerman S V; Bugai A I, Surov Yu N, Lavrushin V F, Pivnenko N S. Zhurnal Prikladnoi Spektroskopii, 1979, 31: 1036

    33. [33]

      [33] Reddy R S, Rosa J N, Veiros L F, Caddick S, Gois P M P. Org Biomol Chem, 2011, 9: 3126

    34. [34]

      [34] Ruiz D M, Romanelli G P, Bennardi D O, Baronetti G T, Thomas H J, Autino J C. ARKIVOC, 2008, 12: 269

    35. [35]

      [35] Munusamy R, Dhathathreyan K S, Balasubramanian K K, Venkatachalam C S. J Chem Soc, Perkin Trans 2, 2001: 1154

  • 加载中
    1. [1]

      Yue Zhao Yanfei Li Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

    2. [2]

      Guojie Xu Fang Yu Yunxia Wang Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060

    3. [3]

      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

    4. [4]

      Baitong Wei Jinxin Guo Xigong Liu Rongxiu Zhu Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003

    5. [5]

      Lihui Jiang Wanrong Dong Hua Yang Yongqing Xia Hongjian Peng Jun Yuan Xiaoqian Hu Zihan Zeng Yingping Zou Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056

    6. [6]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    7. [7]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

    8. [8]

      Shiyan Cheng Yonghong Ruan Lei Gong Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

    9. [9]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    10. [10]

      Yongqing Kuang Jie Liu Jianjun Feng Wen Yang Shuanglian Cai Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

    11. [11]

      Tingbo Wang Yao Luo Bingyan Hu Ruiyuan Liu Jing Miao Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082

    12. [12]

      Yurong Tang Yunren Shi Yi Xu Bo Qin Yanqin Xu Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087

    13. [13]

      Jiaqi ANYunle LIUJianxuan SHANGYan GUOCe LIUFanlong ZENGAnyang LIWenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072

    14. [14]

      Jinyao Du Xingchao Zang Ningning Xu Yongjun Liu Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

    15. [15]

      Chengqian Mao Yanghan Chen Haotong Bai Junru Huang Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

    16. [16]

      Wentao Lin Wenfeng Wang Yaofeng Yuan Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095

    17. [17]

      Daojuan Cheng Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105

    18. [18]

      Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047

    19. [19]

      Yuting Zhang Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037

    20. [20]

      Ruitong Zhang Zhiqiang Zeng Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004

Metrics
  • PDF Downloads(187)
  • Abstract views(658)
  • HTML views(33)

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