Citation: Wang Lu-Ning, Yu Zhi-Xiang. Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Eight-Membered Carbocycles: an Update from 2010 to 2020[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3536-3558. doi: 10.6023/cjoc202010025 shu

Transition-Metal-Catalyzed Cycloadditions for the Synthesis of Eight-Membered Carbocycles: an Update from 2010 to 2020

Wang Lu-Ning ,
Yu Zhi-Xiang ^,

Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871

Corresponding author: Yu Zhi-Xiang, yuzx@pku.edu.cn
Received Date: 16 October 2020
Revised Date: 9 November 2020
Available Online: 11 November 2020

Figures(22)

Eight-membered carbocycles are widely found in natural products with significant biological activities and other molecules ranging from perfumes to potential materials. Therefore, accessing these eight-membered carbocycle embedded molecules is important for drug discovery, biological investigation, fragrance industry, material development and many other fields. However, the synthesis of eight-membered carbocycles is still posing challenges to synthetic chemists. Hence, tremendous efforts have been endeavored by many leading chemists to discover and develop new reactions in order to synthesize eight-membered carbocycles. Among these reactions, transition-metal-catalyzed cycloadditions of [m+n], [m+n+o], [m+ n+o+p] have evolved as powerful tools to achieve this aim. This topic has been reviewed in 2010. Summarized here are many new developments in this field and applications of the previously developed reactions in natural product synthesis since then.
- eight-membered carbocycles,
- transition metal catalysis,
- cycloaddition,
- total synthesis
1. [1]
  (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
  (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
  (c) Yet, L. Chem. Rev. 2000, 100, 2963.
2. [2]
  Suffness, M. Taxol:Science and Applications, CRC Press, Boca Raton, FL, 1995.
3. [3]
  (a) Tang, Y.-Z.; Liu, Y.-H.; Chen, J.-X. Mini-Rev. Med. Chem. 2012, 12, 53.
  (b) Shang, R.; Wang, J.; Guo, W.; Liang, J. Curr. Top. Med. Chem. 2013, 13, 3013.
  (c) Goethe, O.; Heuer, A.; Ma, X.; Wang, Z.; Herzon, S. B. Nat. Prod. Rep. 2019, 36, 220.
4. [4]
  (a) Armanino, N.; Charpentier, J.; Flachsmann, F.; Goeke, A.; Liniger, M.; Kraft, P. Angew. Chem., Int. Ed. 2020, 59, 16310.
  (b) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem., Int. Ed. 2000, 39, 2980.
  (c) Birkbeck, A. A. Challenges in the Synthesis of Natural and Non-Natural Volatiles. In The Chemistry and Biology of Volatiles, Ed.: Herrmann, A., John Wiley & Sons, Ltd., New York, 2010, pp. 173~193.
  (d) Vesley, J. A.; Massie, S. N. US 3985769, 1976.
  (e) Markert, T. WO 99/54430, 1998.
  (f) Fráter, G.; Bajgrowicz, J. A.; Kraft, P. Tetrahedron 1998, 54, 7633.
  (g) Granier, T.; Bajgrowicz, J. A.; Hanhart, A. US 7888309, 2011.
5. [5]
  (a) Martinez, H.; Ren, N.; Matta, M. E.; Hillmyer, M. A. Polym. Chem. 2014, 5, 3507.
  (b) Hill, A. R.; Balogh, J.; Moncho, S.; Su, H.-L.; Tuba, R.; Brothers, E. N.; Al-Hashimi, M.; Bazzi, H. S. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 3137.
6. [6]
  For selected reviews for Diels-Alder reaction in synthesis, see:
  (a) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T. Vassilikogiannakis. G. Angew. Chem., Int. Ed. 2002, 41, 1668.
  (b) Takao, K.-I.; Munakata, R.; Tadano, K.-I. Chem. Rev. 2005, 105, 4779.
  (c) Wessig, P.; Müller, G. Chem. Rev. 2008, 108, 2051.
  (d) Funel, J.-A.; Abele, S. Angew. Chem., Int. Ed. 2013, 52, 3822.
  (e) Jiang, X.; Wang, R. Chem. Rev. 2013, 113, 5515.
  (f) Heravi, M. M.; Vavsari, V. F. RSC Adv. 2015, 5, 50890.
  (g) Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926.
  (h) Tasdelen, M. A. Polym. Chem. 2011, 2, 2133.
7. [7]
  Selected reviews for metal-catalyzed[4+2] reactions:
  (a) Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359.
  (b) Carmona, D.; Lamata, M. P.; Oro, L. A. Coord. Chem. Rev. 2000, 200~202, 717.
  (c) Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255.
  (d) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
  (e) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
  (f) Robinson, J. E. Modern Rhodium-Catalyzed Organic Reactions; Ed.: Evans, P. A., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2005, pp. 241~262.
8. [8]
  (a) Ben-Shoshan, R.; Sarel, S. J. Chem. Soc. D 1969, 883.
  (b) Victor, R.; Ben-Shoshan, R.; Sarel, S. Tetrahedron Lett. 1970, 4253.
  (c) Sarel, S. Acc. Chem. Res. 1978, 11, 204.
  (d) Aumann, R. J. Am. Chem. Soc. 1974, 96, 2631.
  (e) Taber, D. F.; Kanai, K.; Jiang, Q.; Bui, G. J. Am. Chem. Soc. 2000, 122, 6807.
  (f) Taber, D. F.; Joshi, P. V.; Kanai, K. J. Org. Chem. 2004, 69, 2268.
  (g) Kurahashi, T.; de Meijere, A. Synlett 2005, 2619.
  (h) Iwasawa, N.; Owada, Y.; Matsuo, T. Chem. Lett. 1995, 115.
  (i) Owada, Y.; Matsuo, T.; Iwasawa, N. Tetrahedron 1997, 53, 11069.
  (j) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4.
  (k) Shu, D.; Li, X.; Zhang, M.; Robichaux, P. J.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 1346.
  (l) Grabowski, N. A.; Hughes, R. P.; Jaynes, B. S.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1986, 1694.
  (m) Cho, S. H.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2631.
  (n) Semmelhack, M. F.; Ho, S.; Steigerwald, M.; Lee, M. C. J. Am. Chem. Soc. 1987, 109, 4397.
  (o) Brancour, C.; Fukuyama, T.; Ohta, Y.; Ryu, I.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Chem. Commun. 2010, 46, 5470.
  (p) Jiang, G.-J.; Fu, X.-F.; Li, Q.; Yu, Z.-X. Org. Lett. 2012, 14, 692.
  (q) Li, X.; Song, W.; Tang, W. J. Am. Chem. Soc. 2013, 135, 16797.
  (r) Fukuyama, T.; Ohta, Y.; Brancour, C.; Miyagawa, K.; Ryu, I.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Chem.-Eur. J. 2012, 18, 7243.
  (s) Farley, C. M.; Sasakura, K.; Zhou, Y.-Y.; Kanale, V. V.; Uyeda, C. J. Am. Chem. Soc. 2020, 142, 4598.
9. [9]
  (a) Jiao, L.; Lin, M.; Zhuo, L.-G.; Yu, Z.-X. Org. Lett. 2010, 12, 2528.
  (b) Mazumder, S.; Shang, D.; Negru, D. E.; Baik, M.-H.; Evans, P. A. J. Am. Chem. Soc. 2012, 134, 20569.
  (c) Kim, S.; Chung, Y. K. Org. Lett. 2014, 16, 4352.
  (d) Wang, J.; Hong, B.; Hu, D.; Kadonaga, Y.; Tang, R.; Lei, X. J. Am. Chem. Soc. 2020, 142, 2238.
10. [10]
  Selected reviews for metal-catalyzed[2+2+2] reactions:
  (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 539.
  (b) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
  (c) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741.
  (d) Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2011, 40, 3430.
  (e) Shibata, T.; Tsuchikama, K. Org. Biomol. Chem. 2008, 6, 1317.
  (f) Li, C.; Zhang, H.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 3082.
  (g) Shaw, M. H.; Melikhova, E. Y.; Kloer, D. P.; Whittingham, W. G.; Bower, J. F. J. Am. Chem. Soc. 2013, 135, 4992.
11. [11]
  (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
  (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
  (c) Fürstner, A. Top. Catal. 1997, 4, 285.
  (d) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006, 45, 2664.
  (e) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
  (f) Michaut, A.; Rodriguez, J. Angew. Chem., Int. Ed. 2006, 45, 5740.
12. [12]
  Hu, Y.-J.; Li, L.-X.; Han, J.-C.; Min, L.; Li, C.-C. Chem. Rev. 2020, 120, 5910. doi: 10.1021/acs.chemrev.0c00045
13. [13]
  (a) Liang, Y.; Jiang, X.; Yu, Z.-X. Chem. Commun. 2011, 47, 6659.
  (b) Liang, Y.; Jiang, X.; Fu, X.-F.; Ye, S.; Wang, T.; Yuan, J.; Wang, Y.; Yu, Z.-X. Chem.-Asian J. 2012, 7, 593.
14. [14]
  (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
  (b) Galli, C.; Mandolini, L. Eur. J. Org. Chem. 2000, 2000, 3117.
15. [15]
  Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. doi: 10.1021/cr950016l
16. [16]
  Yu, Z.-X.; Wang, Y.; Wang, Y. Chem.-Asian J. 2010, 5, 1072. doi: 10.1002/asia.200900712
17. [17]
  (a) Reed, H. W. B. J. Chem. Soc. 1954, 1931.
  (b) Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 426.
18. [18]
  Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678. doi: 10.1021/ja00275a085
19. [19]
  Park, J. W.; Park, J. E.; Park, J. H.; Hong, M. R.; Kim, S. M.; Chung, Y. K.; Kim, C. H. Synlett 2016, 27, 455.
20. [20]
  Llorente, N.; Fernández-Pérez, H.; Bauzá, A.; Frontera, A.; Vidal-Ferran, A. Catal. Sci. Technol. 2018, 8, 5251. doi: 10.1039/C8CY00684A
21. [21]
  (a) tom Dieck, H.; Dietrich, J. Chem. Ber. 1984, 117, 694.
  (b) tom Dieck, H.; Dietrich, J. Angew.Chem., Int. Ed. 1985, 24, 781.
  (c) Mallien, M.; Haupt, E. T. K.; tom Dieck, H. Angew. Chem., Int. Ed. 1988, 27, 1062.
22. [22]
  Lee, H.; Campbell, M. G.; Sánchez, R. H.; Börgel, J.; Raynaud, J.; Parker, S. E.; Ritter, T. Organometallics 2016, 35, 2923. doi: 10.1021/acs.organomet.6b00474
23. [23]
  Kennedy, C. R.; Zhong, H. Y.; Macaulay, R. L.; Chirik, P. J. J. Am. Chem. Soc. 2019, 141, 8557.
24. [24]
  (a) Braconi, E.; Götzinger, A. C.; Cramer, N. J. Am. Chem. Soc. 2020, 142, 19819.
  (b) Baldenius, K.-U.; tom Dieck, H.; König, W. A.; Icheln, D.; Runge, T. Angew. Chem., Int. Ed. 1992, 31, 305.
25. [25]
  Selected reviews for metal-catalyzed C-C bond activation of strained rings:
  (a) Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100.
  (b) Ruhland, K. Eur. J. Org. Chem. 2012, 2012, 2683.
  (c) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410.
  (d) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
  (e) Cleavage of Carbon-Carbon Single Bonds by Transition Metals, Eds.: Murakami, M.; Chatani, N., Wiley-VCH, Weinheim, Germany, 2016.
  (f) Dong, G. C-C Bond Activation, In Topics in Current Chemistry, Eds.: Bayley, H.; Houk, K. N.; Hughes, G.; Hunter, C. A.; Ishihara, K.; Krische, M. J.; Lehn, J.-M.; Luque, R.; Olivucci, M.; Siegel, J. S.; Thiem, J.; Venturi, M.; Wong, C.-H.; Wong, H. N. C; You, S.-L.; Yam, V. W.-W.; Yan, C. Springer Verlag, Berlin and Heidelberg, Germany, 2014, DOI: 10.1007/978-3-642-55055-3.
  (g)Rubin,M.;Rubina,M.;Gevorgyan,V.Chem.Rev.2007,107,3117.
  (h)Fumagalli,G.;Stanton,S.;Bower,J.F.Chem.Rev.2017,117,9404.
  (i)Dai,H.;Wu,F.;Bai,D.Chin.J.Org.Chem.2020,40,1423(inChinese).
  (代洪雪,吴芬,白大昌,有机化学,2020,40,1423.
26. [26]
  (a) Evans, J. A.; Everitt, G. F.; Kemmitt, R. D. W.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1973, 158.
  (b) Liebeskind, L. S.; Baysdon, S. L.; South, M. S.; Blount, J. F. J. Organomet. Chem. 1980, 202, C73.
  (c) Liebeskind, L. S.; Baysdon, S. L.; South, M. S.; Iyer, S.; Leeds, J. P. Tetrahedron 1985, 41, 5839.
  (d) Huffman, M. A.; Liebeskind, L. S.; Pennington, W. T. Organometallics 1990, 9, 2194.
  (e) Masuda, Y.; Hasegawa, M.; Yamashita, M.; Nozaki, K.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2013, 135, 7142.
  (f) Okumura, S.; Sun, F.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2017, 139, 12414.
  (g) Xu, T.; Dong, G. Angew. Chem., Int. Ed. 2012, 51, 7567.
  (h) Xu, T.; Ko, H. M.; Savage, N. A.; Dong, G. J. Am. Chem. Soc. 2012, 134, 20005.
  (i) Deng, L.; Chen, M.; Dong, G. J. Am. Chem. Soc. 2018, 140, 9652.
  (j) Lu, G.; Fang, C.; Xu, T.; Dong, G.; Liu, P. J. Am. Chem. Soc. 2015, 137, 8274.
  (k) Xu, T.; Savage, N. A.; Dong, G. Angew. Chem., Int. Ed. 2014, 53, 1891.
  (l) Chen, P.-H.; Xu, T.; Dong, G. Angew. Chem., Int. Ed. 2014, 53, 1674.
  (m) Sun, T. W.; Zhang, Y.; Qiu, B.; Wang, Y.; Qin, Y.; Dong, G.; Xu, T. Angew. Chem., Int. Ed. 2018, 57, 2859.
  (n) Deng, L.; Xu, T.; Li, H.; Dong, G. J. Am. Chem. Soc. 2016, 138, 369.
  (o) Chen, P.-H.; Sieber, J.; Senanayake, C. H.; Dong, G. Chem. Sci. 2015, 6, 5440.
  (p) Zhu, Z.; Li, X.; Chen, S.; Chen, P.-H.; Billett, B. A.; Huang, Z.; Dong, G. ACS Catal. 2018, 8, 845.
  (q) Xu, Z.-Y.; Zhang, S.-Q.; Liu, J.-R.; Chen, P.-P.; Li, X.; Yu, H.-Z.; Hong, X.; Fu, Y. Organometallics 2018, 37, 592.
  (r) Bender, M.; Turnbull, B. W. H.; Ambler, B. R.; Krische, M. J. Science 2017, 357, 779.
  (s) Ambler, B. R.; Turnbull, B. W. H.; Suravarapu, S. R.; Uteuliyev, M. M.; Huynh, N. O.; Krische, M. J. J. Am. Chem. Soc. 2018, 140, 9091.
  (t) Deng, L.; Dong, G. Trends in Chem. 2020, 2, 183.
27. [27]
  Juliá-Hernández, F.; Ziadi, A.; Nishimura, A.; Martin, R. Angew. Chem., Int. Ed. 2015, 54, 9537. doi: 10.1002/anie.201503461
28. [28]
  Yang, S.; Xu, Y.; Li, J. Org. Lett. 2016, 18, 6244. doi: 10.1021/acs.orglett.6b02943
29. [29]
  Zou, H.; Wang, Z.-L.; Huang G. Chem.-Eur J. 2017, 23, 12593. doi: 10.1002/chem.201702316
30. [30]
  Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Liebigs Ann. Chem. 1948, 560, 1. doi: 10.1002/jlac.19485600102
31. [31]
  (a) Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2007, 129, 13402.
  (b) Wender, P. A.; Christy, J. P.; Lesser, A. B.; Gieseler, M. T. Angew. Chem., Int. Ed. 2009, 48, 7687.
32. [32]
  Chai, Z.; Wang, H.-F.; Zhao, G. Synlett 2009, 11, 1785.
33. [33]
  Nasrallah, D. J.; Croatt, M. P. Eur. J. Org. Chem. 2014, 2014, 3767. doi: 10.1002/ejoc.201402109
34. [34]
  Greco, A.; Carbonar, A.; Dall'Asta, G. J. Org. Chem. 1970, 35, 271. doi: 10.1021/jo00826a067
35. [35]
  Murakami, M.; Ashida, S.; Matsuda, T. J. Am. Chem. Soc. 2006, 128, 2166. doi: 10.1021/ja0552895
36. [36]
  Tao, J.-Y.; Fang, D.-C.; Chass, G. A. Phys. Chem. Chem. Phys. 2012, 14, 6937. doi: 10.1039/c2cp40067g
37. [37]
  Lainhart, B. C.; Alexanian, E. J. Org. Lett. 2015, 17, 1284. doi: 10.1021/acs.orglett.5b00267
38. [38]
  Gilbertson, S. R.; DeBoef, B. J. Am. Chem. Soc. 2002, 124, 8784. doi: 10.1021/ja026536x
39. [39]
  DeBoef, B.; Counts, W. R.; Gilbertson, S. R. J. Org. Chem. 2007, 72, 799. doi: 10.1021/jo0620462
40. [40]
  Canlas, G. M. R.; Gilbertson, S. R. Chem. Commun. 2014, 50, 5007. doi: 10.1039/C4CC01320D
41. [41]
  (a) Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782.
  (b) Evans, P. A.; Baum, E. W. J. Am. Chem. Soc. 2004, 126, 11150.
  (c) Evans, P. A.; Baum, E. W.; Fazal, A. N.; Pink, M. Chem. Commun. 2005, 63.
42. [42]
  Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2006, 128, 5354. doi: 10.1021/ja060878b
43. [43]
  (a) Hilt, G.; Janikowski, J. Angew. Chem., Int. Ed. 2008, 47, 5243.
  (b) Varela, J. A.; Castedo, L.; Saá, C. Org. Lett. 2003, 5, 2841.
44. [44]
  Yamasaki, R.; Ohashi, M.; Maeda, K.; Kitamura, T.; Nakagawa, M.; Kato, K.; Fujita, T.; Kamura, R.; Kinoshita, K.; Masu, H.; Azumaya, I.; Ogoshi, S.; Saito, S. Chem.-Eur J. 2013, 19, 3415. doi: 10.1002/chem.201204087
45. [45]
  Jiménez, T.; Carreras, J.; Ceccon, J.; Echavarren, A. M. Org. Lett. 2016, 18, 1410. doi: 10.1021/acs.orglett.6b00342
46. [46]
  Davis, R. E.; Dodds, T. A.; Hseu, T. H.; Wagnon, J. C.; Devon, T.; Tancrede, J.; McKennis, J. S.; Pettit, R. J. Am. Chem. Soc. 1974, 96, 7562. doi: 10.1021/ja00831a034
47. [47]
  D'yakonov, V. A.; Kadikova, G. N.; Dzhemilev, U. M. Russ. Chem. Rev. 2018, 87, 797. doi: 10.1070/RCR4793
48. [48]
  (a) Mach, K.; Antropiusová, H.; Sedmera, P.; Hanuš, V.; Tureček, F. J. Chem. Soc., Chem. Commun. 1983, 805.
  (b) Mach, K.; Antropiusová, H.; Petrusová, L.; Hanuš, V.; Tureček, F.; Sedmera, P. Tetrahedron 1984, 40, 3295.
49. [49]
  D'yakonov, V. A.; Kadikova, G. N.; Dzhemilev, U. M. Tetrahedron Lett. 2011, 52, 2780. doi: 10.1016/j.tetlet.2011.03.131
50. [50]
  D'yakonov, V. A.; Kadikova, G. N.; Khalilov, L. M.; Dzhemilev, U. M. Russ. J. Org. Chem. 2013, 49, 1139. doi: 10.1134/S1070428013080071
51. [51]
  Dzhemilev, U. M.; Kadikova, G. N.; Kolokol'tsev, D. I.; D'yakonov, V. A. Tetrahedron 2013, 69, 4609. doi: 10.1016/j.tet.2013.04.019
52. [52]
  (a) D'yakonov, V. A.; Kadikova, G. N.; Kolokol'tsev, D. I.; Ramazanov, I. R.; Dzhemilev, U. M. J. Organomet. Chem. 2015, 794, 23.
  (b) D'yakonov, V. A.; Kadikova, G. N.; Kolokol'tsev, D. I.; Ramazanov, I. R.; Dzhemilev, U. M. Eur. J. Org. Chem. 2015, 2015, 4464.
  (c) D'yakonov, V. A.; Kadikova, G. N.; Nasretdinov, R. N.; Kolokol'tsev, D. I.; Dzhemilev, U. M. Tetrahedron Lett. 2017, 58, 1714.
  (d) D'yakonov, V. A.; Kadikova, G. N.; Khalilov, L. M.; Dzhemilev, U. M. Russ. J. Org. Chem. 2018, 54, 832.
53. [53]
  Achard, M.; Tenaglia, A.; Buono, G. Org. Lett. 2005, 7, 2353. doi: 10.1021/ol050618j
54. [54]
  Achard, M.; Mosrin, M.; Tenaglia, A.; Buono, G. J. Org. Chem. 2006, 71, 2907. doi: 10.1021/jo052630v
55. [55]
  Clavier, H.; Le Jeune, K.; de Riggi, I.; Tenaglia, A.; Buono, G. Org. Lett. 2011, 13, 308. doi: 10.1021/ol102783x
56. [56]
  (a) D'yakonov, V. A.; Kadikova, G. N.; Gazizullina, G. F.; Khalilov, L. M.; Dzhemilev, U. M. Tetrahedron Lett. 2015, 56, 2005.
  (b) D'yakonov, V. A.; Kadikova, G. N.; Gazizullina, G. F.; Dzhemilev, U. M. Russ. Chem. Bull. 2016, 65, 200.
57. [57]
  D'yakonov, V. A.; Kadikova, G. N.; Gazizullina, G. F.; Dzhemilev, U. M. ChemistrySelect 2018, 3, 6221. doi: 10.1002/slct.201801028
58. [58]
  (a) D'yakonov, V. A.; Kadikova, G. N.; Nasretdinov, R. N.; Dzhemileva, L. U.; Dzhemilev, U. M. Eur. J. Org. Chem. 2020, 623.
  (b) Kadikova, G. N.; D'yakonov, V. A.; Nasretdinov, R. N.; Dzhemileva, L. U.; Dzhemilev, U. M. Mendeleev Commun. 2020, 30, 318.
59. [59]
  Oonishi, Y.; Hosotani, A.; Sato, Y. J. Am. Chem. Soc. 2011, 133, 10386. doi: 10.1021/ja203824v
60. [60]
  Oonishi, Y.; Hosotani, A.; Sato, Y. Angew. Chem., Int. Ed. 2012, 51, 11548. doi: 10.1002/anie.201206508
61. [61]
  Liu, T.; Han, L.; Han, S.; Bi, S. Organometallics 2015, 34, 280. doi: 10.1021/om501118e
62. [62]
  (a) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 3470.
  (b) Shi, F.-Q.; Li, X.; Xia, Y.; Zhang, L.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 15503.
  (c) Liang, Y.; Liu, S.; Xia, Y.; Li, Y.; Yu, Z.-X. Chem.-Eur J. 2008, 14, 4361.
  (d) Liang, Y.; Zhou, H.; Yu, Z.-X. J. Am. Chem. Soc. 2009, 131, 17783.
  (e) Liang, Y.; Liu, S.; Yu, Z.-X. Synlett 2009, 905.
  (f) Mercier, E.; Fonovic, B.; Henry, C.; Kwon, O.; Dudding, T. Tetrahedron Lett. 2007, 48, 3617.
  (g) González, I.; Pla-Quintana, A.; Roglans, A.; Dachs, A.; Solà, M.; Parella, T.; Farjas, J.; Roura, P.; Lloveras, V.; Vidal-Gancedo, J. Chem. Commun. 2010, 46, 2944.
  (h) Zhao, L.; Wen, M.; Wang, Z.-X. Eur. J. Org. Chem. 2012, 19, 3587.
63. [63]
  Faustino, H.; Alonso, I.; Mascareñas, J. L.; López, F. Angew. Chem., Int. Ed. 2013, 52, 6526. doi: 10.1002/anie.201302713
64. [64]
  Faustino, H.; Bernal, P.; Castedo, L.; López, F.; Mascareñas, J. L. Adv. Synth. Catal. 2012, 354, 1658. doi: 10.1002/adsc.201200047
65. [65]
  (a) Rigby, J. H.; Henshilwood, J. A. J. Am. Chem. Soc. 1991, 113, 5122.
  (b) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495.
  (c) Rigby, J. H.; Ahmed, G.; Ferguson, M. D. Tetrahedron Lett. 1993, 34, 5397.
  (d) Rigby, J. H.; Sandanayaka, V. P. Tetrahedron Lett. 1993, 34, 935.
  (e) Rigby, J. H.; Pigge, F. C.; Ferguson, M. D. Tetrahedron Lett. 1994, 35, 8131.
  (f) Rigby, J. H.; Sugathapala, P.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 8851.
  (g) Rigby, J. H.; Kondratenko, M. A.; Fiedler, C. Org. Lett. 2000, 2, 3917.
  (h) Rigby, J. H.; Laurent, S. B.; Kamal, Z.; Heeg, M. J. Org. Lett. 2008, 10, 5609.
66. [66]
  Rigby, J. H.; Kirova-Snover, M. Tetrahedron Lett. 1997, 38, 8153. doi: 10.1016/S0040-4039(97)10221-0
67. [67]
  De, S.; Misra, S.; Rigby, J. H. Org. Lett. 2015, 17, 3230. doi: 10.1021/acs.orglett.5b01326
68. [68]
  Magauer, T.; Mulzer, J.; Tiefenbacher, K. Org. Lett. 2009, 11, 5306. doi: 10.1021/ol902263k
69. [69]
  Yao, Z.-K.; Li, J.; Yu, Z.-X. Org. Lett. 2011, 13, 134. doi: 10.1021/ol102700m
70. [70]
  Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 10060. doi: 10.1021/ja072505w
71. [71]
  Jiang, G.-J.; Fu, X.-F.; Li, Q.; Yu, Z.-X. Org. Lett. 2012, 14, 692. doi: 10.1021/ol2031526
72. [72]
  Fu, X.-F.; Xiang, Y.; Yu, Z.-X. Chem.-Eur J. 2015, 21, 4242. doi: 10.1002/chem.201405712
73. [73]
  Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124, 2876. doi: 10.1021/ja0176301
74. [74]
  Wang, Y.; Yu, Z.-X. Acc. Chem. Res. 2015, 48, 2288. doi: 10.1021/acs.accounts.5b00037
75. [75]
  Fan, X.; Zhuo, L.-G.; Tu, Y. Q.; Yu, Z.-X. Tetrahedron 2009, 65, 4709. doi: 10.1016/j.tet.2009.04.020
76. [76]
  Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 4421. doi: 10.1021/ja7100449
77. [77]
  Yuan, C.; Jiao, L.; Yu, Z.-X. Tetrahedron Lett. 2010, 51, 5674. doi: 10.1016/j.tetlet.2010.08.028
78. [78]
  (a) Schuda, P. F.; Phillips, J. L.; Morgan, T. M. J. Org. Chem. 1986, 51, 2742.
  (b) Nishida, M.; Iseki, K.; Shibasaki, M.; Ikegami, S. Chem. Pharm. Bull. 1990, 38, 3230.
  (c) Banwell, M. G.; Austin, K. A. B.; Willis, A. C. Tetrahedron 2007, 63, 6388.
79. [79]
  Fan, X.; Liu, C.-H.; Yu, Z.-X. Rhodium(Ⅰ)-Catalyzed Cycloadditions Involving Vinylcyclopropanes and Their Derivatives. In Rhodium Catalysis in Organic Synthesis, Ed.:Tanaka, K., Wiley-VCH, Weinheim, Germany, 2019, pp. 229~276.
1. [1]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng 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
2. [2]
  Tengfei Xuan , Xinyu Zhang , Wei Han , Yidong Huang , Weiwu Ren . Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B. Chinese Chemical Letters, 2025, 36(2): 109816-. doi: 10.1016/j.cclet.2024.109816
3. [3]
  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
4. [4]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli 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
5. [5]
  Qunlong Zhang , Jingyi Kang , Jingwen Wang , Tiancheng Tan , Zhaoyong Lu . Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G. Chinese Chemical Letters, 2025, 36(3): 109915-. doi: 10.1016/j.cclet.2024.109915
6. [6]
  Peipei CUI , Xin LI , Yilin CHEN , Zhilin CHENG , Feiyan GAO , Xu GUO , Wenning YAN , Yuchen DENG . Transition metal coordination polymers with flexible dicarboxylate ligand: Synthesis, characterization, and photoluminescence property. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2221-2231. doi: 10.11862/CJIC.20240234
7. [7]
  Jingping Hu , Jing Xu . Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C₁₄–epi-deoxycalyciphylline H. Chinese Chemical Letters, 2024, 35(4): 108733-. doi: 10.1016/j.cclet.2023.108733
8. [8]
  Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
9. [9]
  Fengqing Wang , Changxing Qi , Chunmei Chen , Qin Li , Qingyi Tong , Weiguang Sun , Zhengxi Hu , Minyan Wang , Hucheng Zhu , Lianghu Gu , Yonghui Zhang . Discovery and enantioselective total synthesis of antitumor agent asperfilasin A via a regio- and diastereoselective Nazarov cyclization. Chinese Chemical Letters, 2025, 36(6): 110252-. doi: 10.1016/j.cclet.2024.110252
10. [10]
  Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
11. [11]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
12. [12]
  Min Yan , Zihao Ye , Ping Lu . Catalyst-free, visible-light-induced [2π + 2σ] cycloaddition towards azabicyclohexanes. Chinese Chemical Letters, 2025, 36(6): 110540-. doi: 10.1016/j.cclet.2024.110540
13. [13]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
14. [14]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
15. [15]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-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
16. [16]
  Yuqing Liu , Yu Yang , Yuhan E , Changlong Pang , Di Cui , Ang Li . Insight into microbial synthesis of metal nanomaterials and their environmental applications: Exploration for enhanced controllable synthesis. Chinese Chemical Letters, 2024, 35(11): 109651-. doi: 10.1016/j.cclet.2024.109651
17. [17]
  Guoying Han , Qazi Mohammad Junaid , Xiao Feng . Topology-driven directed synthesis of metal-organic frameworks. Chinese Journal of Structural Chemistry, 2025, 44(3): 100447-100447. doi: 10.1016/j.cjsc.2024.100447
18. [18]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
19. [19]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
20. [20]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502

Get Citation

PDF

XML

Metrics

PDF Downloads(24)
Abstract views(3936)
HTML views(485)

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