Citation: Chandrasekar Praveen, Paramasivan T. Perumal. Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes[J]. Chinese Journal of Catalysis, ;2016, 37(2): 288-299. doi: 10.1016/S1872-2067(15)60994-9 shu

Extrapolation of the gold-catalyzed cycloisomerization to the palladium-catalyzed cross-coupling/cycloisomerization of acetylenic alcohols for the synthesis of polysubstituted furans: Scope and application to tandem processes

Chandrasekar Praveen ^a,, ,
Paramasivan T. Perumal ^b

1.
a Functional Materials Division, Central Electrochemical Research Institute (CSIR Laboratory), Karaikudi 630003, India;
2.
b Organic Chemistry Division, Central Leather Research Institute (CSIR Laboratory), Adyar, Chennai 600020, India

Corresponding author: Chandrasekar Praveen,
Received Date: 9 September 2015
Available Online: 12 October 2015
Fund Project:

This paper describes the development of an integrated approach for the preparation of diverse furan derivatives from acetylenic alcohols by gold and palladium catalyzed π-activation chemistry. Notably, this new method was found to be amenable to cyclooctyl-containing substrates, which represents a significant extension to this methodology compared with our previous reports. Furthermore, this newly developed method allowed for the direct construction of cyclooctyl furans from their synthetic precursors under Sonogashira conditions. Experimental results revealed that palladium played two major functions in these reactions, including (1) an essential catalyst in the cross-coupling reaction of the substrates; and (2) facilitating the cyclization of the acetylenic alcohol intermediates through a typical π-activation process. The scope of this chemistry was highlighted by the one-pot synthesis of 3-iodofuran, which provided an opportunity for further functionalization (via coupling methods). Finally, the AuBr₃ protocol was also elaborated to domino cyclization/C-H activation reactions, as well as the cyclization of acyclic precursors. Taken together, the results of this study demonstrate that gold and palladium catalysts can be used to complement each other in cyclization reactions.
- Furan derivatives,
- Cycloisomerization,
- Gold catalysis,
- Palladium catalysis,
- One-pot operation,
- Tandem reactions
1. [1]
  [1] C. H. M. Amijs, C. Ferrer, A. M. Echaverren, Chem. Commun., 2007, 698.
2. [2]
  [2] A. Hoffmann-Roder, N. Krause, Org. Biomol. Chem., 2005, 3, 387.
3. [3]
  [3] A. S. K. Hashmi, Angew. Chem. Int. Ed., 2005, 44, 6990.
4. [4]
  [4] A. Arcadi, S. Di Giuseppe, Curr. Org. Chem., 2004, 8, 795.
5. [5]
  [5] R. A. Widenhoefer, X. Q. Han, Eur. J. Org. Chem., 2006, 4555.
6. [6]
  [6] H. C. Shen, Tetrahedron, 2008, 64, 7847.
7. [7]
  [7] Z. G. Li, C. Brouwer, C. He, Chem. Rev., 2008, 108, 3289.
8. [8]
  [8] L. M. Zhang, J. W. Sun, S. A. Kozmin, Adv. Synth. Catal., 2006, 348, 2271.
9. [9]
  [9] N. Asao, Synlett, 2006, 1645.
10. [10]
  [10] S. M. Ma, S. C. Yu, Z. H. Gu, Angew. Chem. Int. Ed., 2006, 45, 200.
11. [11]
  [11] A. M. Echavarren, C. Nevado, Chem. Soc. Rev., 2004, 33, 431.
12. [12]
  [12] G. Dyker, Angew. Chem. Int. Ed., 2000, 39, 4237.
13. [13]
  [13] A. S. K. Hashmi, Gold Bull., 2004, 37, 51.
14. [14]
  [14] R. Skouta, C. J. Li, Tetrahedron, 2008, 64, 4917.
15. [15]
  [15] N. D. Shapiro, F. D. Toste, Synlett, 2010, 675.
16. [16]
  [16] A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed., 2006, 45, 7896.
17. [17]
  [17] D. J. Gorin, F. D. Toste, Nature, 2007, 446, 395.
18. [18]
  [18] A. S. K. Hashmi, Chem. Rev., 2007, 107, 3180.
19. [19]
  [19] A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed., 2007, 46, 3410.
20. [20]
  [20] M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev., 2012, 41, 2448.
21. [21]
  [21] A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev., 2008, 37, 1766.
22. [22]
  [22] E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun., 2007, 333.
23. [23]
  [23] A. S. K. Hashmi, Gold Bull., 2003, 36, 1.
24. [24]
  [24] C. Praveen, P. Kiruthiga, P. T. Perumal, Synlett, 2009, 1990.
25. [25]
  [25] C. Praveen, S. Jegatheesan, P. T. Perumal, Synlett, 2009, 2795.
26. [26]
  [26] C. Praveen, A. Kalyanasundaram, P. T. Perumal, Synlett, 2010, 777.
27. [27]
  [27] C. Praveen, Y. W. Sagayaraj, P. T. Perumal, Tetrahedron Lett., 2009, 50, 644.
28. [28]
  [28] C. Praveen, K. Karthikeyan, P. T. Perumal, Tetrahedron, 2009, 65, 9244.
29. [29]
  [29] Y. P. Zhu, J. J. Yuan, Y. T. Li, M. Gao, L. P. Cao, J. Y. Ding, A. X. Wu, Synlett, 2011, 52.
30. [30]
  [30] C. Praveen, A. Ayyanar, P. T. Perumal, Bioorg. Med. Chem. Lett., 2011, 21, 4170.
31. [31]
  [31] H. Gasper, S. Santos, M. Carbone, A. S. Rodrigues, A. I. Rodrigues, M. J. Uriz, S. M. S. Feio, D. Melck, M. Humanes, M. Gavagnin, J. Nat. Prod., 2008, 71, 2049.
32. [32]
  [32] H. Hikino, Y. Hikino, I. Yosioka, Chem. Pharm. Bull., 1964, 12, 755.
33. [33]
  [33] R. C. Cambie, P. S. Rutledge, X. S. Yang, P. R. Bergquist, J. Nat. Prod., 1998, 61, 1416.
34. [34]
  [34] M. Gavagnin, E. Mollo, F. Castelluccio, A. Crispino, G. Cimino, J. Nat. Prod., 2003, 66, 1517.
35. [35]
  [35] H. Inouye, H. Matsumara, M. Kawasaski, K. Inoue, M. Tsukada, M. Tabata, Phytochemistry, 1981, 20, 1701.
36. [36]
  [36] M. Kobayashi, A. Muroyama, H. Nakamura, J. Kobayashi, Y. Ohizumi, J. Pharmacol. Exp. Ther., 1991, 257, 90.
37. [37]
  [37] H. Sakamoto, K. I. Furukawa, K. Matsunaga, H. Nakamura, Y. Ohizumi, Biochemistry, 1995, 34, 12570.
38. [38]
  [38] W. L. Xiao, H. J. Zhu, Y. H. Shen, R. T. Li, S. H. Li, H. D. Sun, Y. T. Zheng, R. R. Wang, Y. Lu, C. Wang, Q. T. Zheng, Org. Lett., 2005, 7, 2145.
39. [39]
  [39] N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem., 2005, 70, 4531.
40. [40]
  [40] T. L. Yao, X. X. Zhang, R. C. Larock, J. Am. Chem. Soc., 2004, 126, 11164.
41. [41]
  [41] S. Goncalves, A. Wagner, C. Mioskowski, R. Baati, Tetrahedron Lett., 2009, 50, 274.
42. [42]
  [42] M. Yoshida, M. Al-Amin, K. Matsuda, K. Shishido, Tetrahedron Lett., 2008, 49, 5021.
43. [43]
  [43] J. L. Zhang, H. G. Schmalz, Angew. Chem. Int. Ed., 2006, 45, 6704.
44. [44]
  [44] A. S. K. Hashmi, L. Schwarz, J. H. Choi, T. M. Frost, Angew. Chem. Int. Ed., 2000, 39: 2285.
45. [45]
  [45] C. H. Oh, V. R. Reddy, A. Kim, C. Y. Rhim, Tetrahedron Lett., 2006, 47, 5307.
46. [46]
  [46] G. Mehta, N. S. Likhite, Tetrahedron Lett., 2008, 49, 7113.
47. [47]
  [47] H-K Yim, Y. Liao, H. N. C. Wong, Tetrahedron, 2003, 59, 1877.
48. [48]
  [48] A. Chakraborty, G. K. Kar, J. K. Ray, Tetrahedron, 1997, 53, 2989.
49. [49]
  [49] K. Harada, Y. Tonoi, H. Kato, Y. Fukuyama, Tetrahedron Lett., 2002, 43, 3829.
50. [50]
  [50] R. E. Patre, S. Gawas, S. Sen, P. S. Parameswaran, S. G. Tilve, Tetrahedron Lett., 2007, 48, 3517.
51. [51]
  [51] J. S. Foot, A. T. Phillis, P. P. Sharp, A. C. Wills, M. G. Banwell, Tetrahedron Lett., 2006, 47, 6817.
52. [52]
  [52] G. Blay, L. Cardona, B. Garca, J. R. Pedro, J. J. Snchez, J. Org. Chem., 1996, 61, 3815.
53. [53]
  [53] M. Inoue, A. J. Frontier, S. J. Danishefsky, Angew. Chem. Int. Ed., 2000, 39, 761.
54. [54]
  [54] M. Yoshida, M. Al-Amin, K. Shishido, Synthesis, 2009, 2454.
55. [55]
  [55] A. Blanc, K. Tenbrink, J. M. Weibel, P. Pale, J. Org. Chem., 2009, 74, 5342.
56. [56]
  [56] S. Borghèse, B. Louis, A. Blanc, P. Pale, Catal. Sci. Technol., 2011, 1, 981.
57. [57]
  [57] C. Praveen, C. Iyyappan, P. T. Perumal, Tetrahedron Lett., 2010, 51, 4767.
58. [58]
  [58] C. Praveen, C. Iyyappan, K. Girija, K. S. Kumar, P. T. Perumal, J. Chem. Sci., 2012, 124, 451.
59. [59]
  [59] C. Praveen, A. Ayyanar, P. T. Perumal, Bioorg. Med. Chem. Lett., 2011, 21, 4072.
60. [60]
  [60] C. Praveen, P. DheenKumar, D. Muralidharan, P. T. Perumal, Bioorg. Med. Chem. Lett., 2010, 20, 7292.
61. [61]
  [61] K. Parthasarathy, C. Praveen, C. Balachandran, P. S. Kumar, S. Ignacimuthu, P. T. Perumal, Bioorg. Med. Chem. Lett., 2013, 23, 2708.
62. [62]
  [62] K. Parthasarathy, C. Praveen, P. S. Kumar, C. Balachandran, P. T. Perumal, RSC Adv., 2015, 5, 15818.
63. [63]
  [63] C. Praveen, S. Narendiran, P. Dheenkumar, P. T. Perumal, J. Chem. Sci., 2013, 125, 1543.
64. [64]
  [64] C. R. Johnson, J. P. Adams, M. P. Braun, C. B. W. Senanayake, P. M. Wovkulich, M. R. Uskokoviḉ, Tetrahedron Lett., 1992, 33, 917.
65. [65]
  [65] D. K. Mohapatra, B. Chatterjee, M. K. Gurjar, Tetrahedron Asymmetry, 2008, 19, 1568.
66. [66]
  [66] C. K. Sha, S. J. Huang, Z. P. Zhan, J. Org. Chem., 2002, 67, 831.
67. [67]
  [67] A. L. Germal, J. L. Luche, J. Am. Chem. Soc., 1981, 103, 5454.
68. [68]
  [68] A. Mayasundari, D. G. J. Young, Tetrahedron Lett., 2001, 42, 203.
69. [69]
  [69] K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett., 1975, 16, 4467.
70. [70]
  [70] R. Chinchilla, C. Nájera, Chem. Rev., 2007, 107, 874.
71. [71]
  [71] E. Fillion, R. L. Beingessner, J. Org. Chem., 2003, 68, 9485.
72. [72]
  [72] L. A. Paquette, J. Ezquerra, W. He, J. Org. Chem., 1995, 60, 1435.
73. [73]
  [73] A. B. Neef, C. Schultz, Angew. Chem. Int. Ed., 2009, 48, 1498.
74. [74]
  [74] A. E. Sadak, T. Arslan, N. Celebioglu, N. Saracoglu, Tetrahedron, 2010, 66, 3214.
75. [75]
  [75] C. B. Reese, A. Shaw, J. Chem. Soc. Perkin Trans. 1, 1975, 2422.
76. [76]
  [76] G. Zeni, R. C. Larock, Chem. Rev., 2006, 106, 4644.
77. [77]
  [77] T. W. Lyons, M. S. Sanford, Chem. Rev., 2010, 110, 1147.
78. [78]
  [78] A. Bacchi, M. Costa, N. Della Cá, M. Fabbricatore, A. Fazio, B. Gabriele, C. Nasi, G. Salerno, Eur. J. Org. Chem., 2004, 574.
79. [79]
  [79] A. Arcadi, S. Cacchi, M. D. Rosario, G. Fabrizi, F. Marinelli, J. Org. Chem., 1996, 61, 9280.
80. [80]
  [80] B. Gabriele, G. Salerno, A. Fazio, R. Pittelli, Tetrahedron, 2003, 59, 6251.
81. [81]
  [81] P. Peng, B. X. Tang, S. F. Pi, Y. Liang, J. H. Li, J. Org. Chem., 2009, 74, 3569.
82. [82]
  [82] R. D. Stephens, C. E. Castro, J. Org. Chem., 1963, 28, 3313.
83. [83]
  [83] E. Negishi, Acc. Chem. Res., 1982, 15, 340.
84. [84]
  [84] E. Erdik, Tetrahedron, 1992, 48, 9577.
85. [85]
  [85] M. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457.
86. [86]
  [86] J. K. Stille, Angew. Chem. Int. Ed., 1986, 25, 508.
87. [87]
  [87] H. A. Dieck, R. F. Heck, J. Am. Chem. Soc., 1974, 96, 1133.
88. [88]
  [88] G. Dyker, E. Muth, A. S. K. Hashmi, L. Ding, Adv. Synth. Catal., 2003, 345, 1247.
89. [89]
  [89] M. T. Reetz, K. Sommer, Eur. J. Org. Chem., 2003, 3485.
90. [90]
  [90] J. A. Marshal, B. G. Shearer, S. L. Crooks, J. Org. Chem., 1987, 52, 1236.
91. [91]
  [91] S. Kulyk, W. G. Dougherty Jr., W. S. Kassel, M. J. Zdilla, S. McN. Sieburth, Org. Lett., 2011, 13, 2180.
1. [1]
  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
2. [2]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
3. [3]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
8. [8]
  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
9. [9]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
10. [10]
  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
11. [11]
  Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
12. [12]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
13. [13]
  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
14. [14]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
15. [15]
  Xueting Cao , Shuangshuang Cha , Ming Gong . 电催化反应中的界面双电层：理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041
16. [16]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
17. [17]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
18. [18]
  Haodong JIN , Qingqing LIU , Chaoyang SHI , Danyang WEI , Jie YU , Xuhui XU , Mingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048
19. [19]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
20. [20]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(639)
HTML views(103)

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