近十年Dendralenes催化合成研究进展
收稿日期: 2020-08-13
修回日期: 2020-09-03
网络出版日期: 2020-09-22
基金资助
江苏省自然科学基金面上项目(BK20191305); 南京农业大学中央高校基本科研业务费专项基金(KYDZ201904); 江苏省教育厅“青蓝工程”资助项目
Recent Progress in the Synthesis of Dendralenes: A Decade Update
Received date: 2020-08-13
Revised date: 2020-09-03
Online published: 2020-09-22
Supported by
Natural Science Foundation of Jiangsu Province(BK20191305); Fundamental Research Funds for the Central Universities of Nanjing Agricultural University(KYDZ201904); Qing-Lan Project of Jiangsu Provincial Department of Education
祝洁 , 杨文超 , 张乘运 , 吴磊 . 近十年Dendralenes催化合成研究进展[J]. 有机化学, 2021 , 41(3) : 1081 -1097 . DOI: 10.6023/cjoc202008024
Dendralenes, also known as acyclic, branched and cross-conjugated polyenes, represent an important class of hydrocarbons. Serving as basic motifs for a number of natural products and photolectric materials as well as key intermediates in the rapid synthesis of polycyclic compounds, dendralenes have recently played a prominent part in the area of material chemistry, polymer chemistry, synthetic chemistry and so on. The study on dendralenes has long been neglected but received renewed attention and witnessed rapid development in recent years. The advanced syntheses of dendralenes in the last decade are summarized and organized in order of the number of conjugated units. The synthetic design and mechanism are highlighted in this review with their future development on synthesis and application proposed as well.
Key words: dendralenes; conjugated polyenes; cumulenes; coupling; cyclization; derivate
[1] | (a) Hopf, H. Angew. Chem.. Int. Ed. 1984, 23, 948. |
[1] | (b) Hopf, H. Nature 2009, 460, 183. |
[1] | (c) Hopf, H. Angew. Chem., Int. Ed. 2001, 40, 705. |
[1] | (d) Sherburn, M. S. Acc. Chem. Res. 2015, 48, 1961. |
[1] | (e) Hopf, H.; Sherburn, M. S. Cross Conjugation-Modern Dendralene, Radialene and Fulvene Chemistry, Wiley-VCH, Verlag GmbH & Co. KGaA, 2016. |
[2] | Hopf, H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, Wiley-VCH, Weinheim, 2000, p. 103. |
[3] | Paul, R.; Tchelitcheff, S. C. R. Hebd. Seances Acad. Sci. 1951, 232, 1939. |
[4] | (a) Bolmquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1955, 77, 81;. |
[4] | (b) Bailey, W. J.; Ecomomy, J. J. Am. Chem. Soc. 1955, 77, 1133;. |
[4] | (c) Bailey, W. J.; Nielsen, N. A. J. Org. Chem. 1962, 27, 3088. |
[5] | (a) Bradford, T. A.; Payne, A. D.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. J. Org. Chem. 2010, 75, 491. |
[5] | (b) Hopf, H.; Sherburn, M. S. Angew. Chem.. Int. Ed. 2012, 51, 2298. |
[5] | (c) Naidua, G. S.; Singh, R. Ghosh, S. K. Synlett 2018, 29, 282. |
[6] | Fielder, S.; Rowan, D. D.; Sherburn, M. S. Angew. Chem., Int. Ed. 2000, 39, 4331. |
[7] | Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. |
[8] | Miller, N. A.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. Angew. Chem., Int. Ed. 2007, 46, 937. |
[9] | Payne, A. D.; Bojase, G.; Paddon-Row, M. N.; Sherburn, M. S. Angew. Chem., Int. Ed. 2009, 48, 4836. |
[10] | (a) Stehling, L.; Wilke, G. Angew. Chem.. Int. Ed. 1988, 27, 571. |
[10] | (b) Payne, A. D.; Willis, A. C.; Sherburn, M. S. J. Am. Chem. Soc. 2005, 127, 12188. |
[10] | (c) Pellissier, H. Tetrahedron 2005, 61, 6479. |
[10] | (d) Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577. |
[10] | (e) Tius, M. A. Eur. J. Org. Chem. 2005,2193. |
[10] | (f) Pronin, S. V.; Shenvi, R. A. J. Am. Chem. Soc. 2012, 134, 19604;. 39ef1d2f-797f-4223-b3ac-b34dd9f23b4f |
[10] | (g) Fallon, T.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S. J. Org. Chem. 2014, 79, 3185. |
[10] | (h) Desfeux, C.; Besnard, C.; Mazet, C. Org. Lett. 2020, 22, 8181. |
[11] | (a) Bloomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1955, 77, 81. |
[11] | (b) Bailey, W. J.; Economy, J. J. Am. Chem. Soc. 1955, 77, 1133. |
[11] | (c) Bloomquist, A. T.; Verdol, J. A. J. Am. Chem. Soc. 1955, 77, 1806. |
[11] | (d) Bailey, W. J.; Cunov, C. H.; Nicholas, L. J. Am. Chem. Soc. 1955, 77, 2787. |
[11] | (e) Martin, H. D.; Echert-Macsic, M.; Mayer, B. Angew. Chem.. Int. Ed. 1980, 19, 807. |
[11] | (f) Hopf, H. Angew. Chem.. Int. Ed. 1982, 21, 286. |
[11] | (g) Hopf, H. Angew. Chem.. Int. Ed. 1984, 96, 947. |
[11] | (h) Brain, P. T.; Smart, B. A.; Robertson, H. E.; Davis, M. J.; H. Rankin, D. W.; Henry, W. J.; Gosney, I. J. Org. Chem. 1997, 62, 2767. |
[11] | (i) Woo, S.; Squires, N.; Fallis, A. G. Org. Lett. 1999, 1, 573. |
[11] | (j) Woo, S.; Legoupy, S.; Parra, S.; Fallis, A. G. Org. Lett. 1999, 1, 1013. |
[11] | (k) Le N?tre, J.; Martinez,, A. A.; Dixneuf,, P. H.; Bruneau,, C. Tetrahedron 2003, 59, 9425. |
[11] | (l) Park, S.; Lee, D. Synthesis 2007,2313. |
[12] | (a) Shimizu, M.; Kurahashi, T.; Shimono, K.; Tanaka, K.; Nagao, I.; Kiyomoto, S.; Hiyama, T. Chem.-Asian J. 2007, 2, 1400. |
[12] | (b) Bojase, G.; Payne, A. D.; Willis, A. C.; Sherburn, M. S. Angew. Chem.. Int. Ed. 2008, 47, 910. |
[13] | George, J.; Ward, J. S.; Sherburn, M. S. Chem. Sci. 2019, 10, 9969. |
[14] | Ghosh, S. K.; Singh, R.; Date, S. M. Chem. Commun. 2003,636. |
[15] | Singh, R.; Ghosh, S. K. Chem. Commun. 2011, 47, 10809. |
[16] | (a) Singh, R.; Naidu, G. S.; Ghosh, S. K. Proc. Natl. Acad. Sci.. India, Sect. A Phys. Sci. 2016, 86, 619. |
[16] | (b) Naidu, G. S.; Singh, R.; Kumarb, M.; Ghosh, S. K. RSC Adv. 2016, 6, 37136. |
[17] | Rahif, M.; Roux, M.; Thibonnet, J.; Parrain, J.-L. Mol. Diversity 2013, 17, 49. |
[18] | (a) Ma, S. Chem. Rev. 2005, 105, 2829. |
[18] | (b) Ye, J.; Ma, S. Acc. Chem. Res. 2014, 47, 989. |
[18] | (c) Jia, M.; Ma, S. Angew. Chem.. Int. Ed. 2016, 55, 9134. |
[19] | Wang, H.; Beiring, B.; Yu, D.-G.; Collins, K. D.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12430. |
[20] | Qiu, Y.; Posevins, D.; B?ckvall, J.-E. Angew. Chem., Int. Ed. 2017, 56, 13112. |
[21] | Zhang, T.; Song, C.; Meng, Y.; Chen, P.; Xu, H.; Chang, J. J. Org. Chem. 2017, 82, 9905. |
[22] | (a) Lu, X.-Y.; Zhang, C.-M.; Xu, Z.-R. Acc. Chem. Res. 2001, 34, 535. |
[22] | (b) Cowen, B. J.; Miller, C. J. Chem. Soc. Rev. 2009, 38, 3102. |
[22] | (c) Pei, C.-K. Shi, M. Chem.-Eur. J. 2012, 18, 6712. 42d445b1-4d74-44a8-ae66-c143c537e548 |
[23] | (a) Yang, Y.; Qiu, X.; Zhao, Y.; Mu, Y.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 495. |
[23] | (b) Yang, Y.; Li, R.; Zhao, Y.; Zhao, D.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 8743. |
[24] | Mao, M.; Zhang, L.; Chen, Y.-Z.; Zhu, J.; Wu, L. ACS Catal. 2017, 7, 181. |
[25] | Xia, Y.-T.; Xie, X.-Y.; Cui, S.-H.; Ji, Y.-G.; Wu, L. Chem. Commun. 2019, 55, 11699. |
[26] | Xia, Y.-T.; Wu, J.-J.; Zhang, C.-Y.; Mao, M.; Ji, Y.-G.; Wu, L. Org. Lett. 2019, 21, 6383. |
[27] | Rivera-Chao, E.; Fa?anás-Mastral, M. Angew. Chem., Int. Ed. 2018, 57, 9945. |
[28] | Li, H.; Gontla, R.; Flegel, J.; Merten, C.; Ziegler, S.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2019, 58, 307. |
[29] | Frank, B. B.; Kivala, M.; Blanco, B. C.; Breiten, B.; Schweizer, W. B.; Laporta, P. R.; Biaggio, I.; Jahnke, E.; Tykwinski, R. R.; Boudon, C.; Gisselbrecht, J.-P.; Diederich, F. Eur. J. Org. Chem. 2010,2487. |
[30] | Yamauchi, T.; Shibata, Y.; Aki, T.; Yoshimura, A.; Yao, M.; Misaki, Y. Chem. Lett. 2018, 47, 1176. |
[31] | Januszewski, J. A.; Hampel, F.; Neiss, C.; G?rling, A.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2014, 53, 3743. |
[32] | Saglam, M. F.; Fallon, T.; Paddon-Row, M. N.; Sherburn, M. S. J. Am. Chem. Soc. 2016, 138, 1022. |
[33] | Polák, P.; Tobrman, T. Eur. J. Org. Chem. 2019,957. |
[34] | Lippincott, D. J.; Linstadt, R. T. H.; Maser, M. R.; Lipshutz, B. H. Angew. Chem., Int. Ed. 2017, 56, 847. |
[35] | (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. |
[35] | (b) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586. |
[35] | (c) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271. |
[35] | (d) Clay, J. M.; Vedejs, E. J. Am. Chem. Soc. 2005, 127, 5766. |
[35] | (e) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890. |
[36] | Deng, Y.; Bartholomeyzik, T.; Persson, A. K. ?.; Sun, J.; B?ckvall, J.-E. Angew. Chem., Int. Ed. 2012, 51, 2703. |
[37] | Deng, Y.; Bartholomeyzik, T.; B?ckvall, J.-E. Angew. Chem., Int. Ed. 2013, 52, 6283. |
[38] | Bartholomeyzik, T.; Pendrill, R.; Lihammar, R.; Jiang, T.; Widmalm, G.; B?ckvall, J.-E. J. Am. Chem. Soc. 2018, 140, 298. |
[39] | Volla, C.; M., R.; Ba?ckvall, J.-E. Angew. Chem., Int. Ed. 2013, 52, 14209. |
[40] | Volla, C. M. R.; Mazuela, J.; Ba?ckvall, J.-E. Chem.-Eur. J. 2014, 20, 7608. 612af94e-9bb6-475a-b483-a43afb87ebb1 |
[41] | Yang, B.; Qiu, Y.; B?ckvall, J.-E. Acc. Chem. Res. 2018, 51, 1520. |
[42] | Volla, C. M. R.; B?ckvall, J.-E. ACS Catal. 2016, 6, 6398. |
[43] | Zhu, C.; Yang, B.; Qiu, Y.; B?ckvall, J.-E. Angew. Chem., Int. Ed. 2016, 55, 14405. |
[44] | Naidu, V. R.; Posevins, D.; Volla, C. M. R.; B?ckvall, J.-E. Angew. Chem., Int. Ed. 2017, 56, 1590. |
[45] | Jonek, A.; Berger, S.; Haak, E. Chem.-Eur. J. 2012, 18, 15504. 626a977e-2498-4edb-bb1b-ae34a1d2499a |
[46] | Thies, N.; Haak, E. Angew. Chem., Int. Ed. 2015, 54, 4097. |
[47] | Sakashita, K.; Shibata, Y.; Tanaka, K. Angew. Chem., Int. Ed. 2016, 55, 6753. |
[48] | Li, L.; Luo, P.; Deng, Y.; Shao, Z. Angew. Chem., Int. Ed. 2019, 58, 4710. |
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