SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 10: 3327 - 3337

DOI: https://doi.org/10.6023/cjoc202005050

研究论文

(NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用

  • 雍学锋 ,
  • 黄建强 ,
  • 何振宇
展开
  • a 哈尔滨工业大学化学与化工学院 哈尔滨 150001;
    b 深圳格拉布斯研究院 广东深圳 518055;
    c 广东省催化化学重点实验室 广东深圳 518055;
    d 南方科技大学化学系 广东深圳 518055

收稿日期: 2020-05-19

  修回日期: 2020-07-02

  网络出版日期: 2020-07-17

基金资助

广东省基础与应用基础研究基金-青年基金（No.2019A1515110001）资助项目.

收起

Applications of (NHC)Ni(II) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades

  • Yong Xue-Feng ,
  • Huang Jian-Qiang ,
  • Ho Chun-Yu
Expand
  • a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001;
    b Shenzhen Grubbs Institute, Shenzhen, Guangdong 518055;
    c Guangdong Provincial Key Laboratory of Catalysis, Shenzhen, Guangdong 518055;
    d Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received date: 2020-05-19

  Revised date: 2020-07-02

  Online published: 2020-07-17

Supported by

Project supported by the Guangdong Basic and Applied Basic Research Foundation-Youth Project (No. 2019A1515110001).

Fold

摘要

着重研究近期发展的环张力烯烃[3+2]氢烯化重排串联反应（HARC）在合成方面的应用，比较了此类多取代环戊二烯和亚甲基环戊烷的合成机理与传统烯烃和二烯交叉氢烯化反应的不同，并以环化产物为关键原料，进行了包括Diels-Alder、环氧化、臭氧解、卤代重排和氟羟基化等一系列衍生化，一步或多步串联制备了具有高度非对映选择性的、传统方法难以获取的若干有趣且复杂的碳骨架产物.

关键词： 张力烯烃; [3+2]环加成; 氮杂环卡宾; 镍催化; 交叉氢烯化

本文引用格式

雍学锋 , 黄建强 , 何振宇 . (NHC)Ni(II)催化的[3+2]氢烯化重排串联反应的应用[J]. 有机化学, 2020 , 40(10) : 3327 -3337 . DOI: 10.6023/cjoc202005050

Abstract

Synthetic applications of the recently developed (NHC)Ni(Ⅱ) catalyzed[3+2] hydroalkenylation-rearrangement cascade (HARC) were investigated. The foundations of these highly substituted cyclopentadienes and methylene cyclopentanes formation were compared with typical cross-hydroalkenylation of alkenes and dienes. The desired cyclization products were examined as key starting materials for a range of olefin functionalization methodology, including Diels-Alder, epoxidation, ozonolysis, halogenation-rearrangement and fluorohydroxylation. The results showed that several very interesting carbon skeletons can be obtained easily with high diastereoselectivity in one step or in cascade.

Key words： strained alkene; [3+2] cycloaddition; N-heterocycle carbenes; Ni catalysis; cross-hydroalkenylation

参考文献

[1] (a) Romano, C.; Mazet, C. J. Am. Chem. Soc. 2018, 140, 4743.
(b) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
[2] Wilke, G. Angew. Chem. Int. Ed. 1988, 27, 185.
[3] Bogdanović, B.; Spliethoff, B.; Wilke, G. Angew. Chem. Int. Ed. 1980, 19, 622.
[4] (a) Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095.
(b) Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G. Tetrahedron:Asymmetry 1992, 3, 163.
[5] Ziegler, K.; Cellert, H. G.; Holzkamp, E.; Wilke, G. Brennst. Chem. 1954, 35, 321.
[6] (a) Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. Int. Ed. 1955, 67, 426.
(b) Wilke, G. Angew. Chem. Int. Ed. 1957, 69, 397.
(c) Wilke, G. Angew. Chem. Int. Ed. 1960, 72, 581.
(d) Wilke, G.; Bogdanov. B. Angew. Chem. Int. Ed. 1961, 73, 756.
(e) Wilke, G.; Kroner, M.; Bogdanov, B Angew. Chem. Int. Ed. 1961, 73, 755.
(f) Wilke, G.; Herrmann, G. Angew. Chem. Int. Ed. 1966, 5, 581.
(g) Bogdanov. B; Wilke, G. Brennst.-Chem. 1968, 49, 323.
[7] RajanBabu, T. V. Chem. Rev. 2003, 103, 2845.
[8] Kawata, N.; Maruya, K.-i.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 3217.
[9] (a) Ceder, R.; Muller, G.; Ordinas, J. I. J. Mol. Catal. 1994, 92, 127.
(b) Monteiro, A. L.; Seferin, M.; Dupont, J.; de Souza, R. F. Tetrahedron Lett. 1996, 37, 1157.
(c) Wegner, A.; Leitner, W. Chem. Commun. 1999, 1583.
(d) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459.
[10] (a) Shi, W.-J.; Zhang, Q.; Xie, J.-H.; Zhu, S.-F.; Hou, G.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 2780.
(b) Zhang, Q.; Zhu, S.-F.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2008, 350, 1507.
(c) Zhang, Q.; Zhu, S.-F.; Cai, Y.; Wang, L.-X.; Zhou, Q.-L. Sci. China Chem. 2010, 53, 1899.
[11] Li, K.; Li, M.-L.; Zhang, Q.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2018, 140, 7458.
[12] Clement, N. D.; Cavell, K. J. Angew. Chem. Int. Ed. 2004, 43, 3845.
[13] Ho, C.-Y.; He, L. Angew. Chem. Int. Ed. 2010, 49, 9182.
[14] Ho, C.-Y.; Chan, C.-W.; He, L. Angew. Chem. Int. Ed. 2015, 54, 4512.
[15] Ho, C.-Y.; He, L. Chem. Commun. 2012, 48, 1481.
[16] (a) Lian, X.; Chen, W.; Dang, L.; Li, Y.; Ho, C.-Y. Angew. Chem. Int. Ed. 2017, 56, 9048.
(b) Chen, Y.; Dang, L.; Ho, C.-Y. Nat. Commun. 2020, 11, 2269.
[17] Chen, W.; Li, Y.; Chen, Y.; Ho, C.-Y. Angew. Chem. Int. Ed. 2018, 57, 2677.
[18] Ho, C.-Y.; He, L. J. Org. Chem. 2014, 79, 11873.
[19] Huang, J.-Q.; Ho, C.-Y. Angew. Chem. Int. Ed. 2019, 58, 5702.
[20] Huang, J.-Q.; Ho, C.-Y. Angew. Chem. Int. Ed. 2020, 59, 5288.
[21] Kumareswaran, R.; Nandi, M.; RajanBabu, T. V. Org. Lett. 2003, 5, 4345.
[22] Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
[23] (a) Zhang, G.-P.; Huang, S.; Jiang, Y.-J.; Liu, X.-Y.; Ding, C.-H.; Wei, Y.; Hou, X.-L. Chem. Commun. 2019, 55, 6449.
(b) Huang, J.-Q.; Liu, W.; Zheng, B.-H.; Liu, X. Y.; Yang, Z.; Ding, C.-H.; Li, H.; Peng, Q.; Hou, X.-L. ACS Catal. 2018, 8, 1964.
(c) Huang, J.-Q.; Zhao, J.-F.; Yang, Z.; Ding, C.-H.; Hou, X.-L.; Peng, X.-S.; Wong, H. N. C. Asian J. Org. Chem. 2017, 6, 1769.
(d) Huang, J.-Q.; Ding, C.-H.; Hou, X.-L. J. Org. Chem. 2014, 79, 12010.
(e) Liu, W.; Chen, D.; Zhu, X.-Z.; Wan, X.-L.; Hou, X.-L. J. Am. Chem. Soc. 2009, 131, 8734.
[24] (a) Fumagalli, G.; Stanton, S.; Bower, J. F. Chem. Rev. 2017, 117, 9404.
(b) Simaan, M.; Marek, I. Angew. Chem. Int. Ed. 2018, 57, 1543.
(c) Wang, X.-B.; Zheng, Z.-J.; Xie, J.-L.; Gu, X.-W.; Mu, Q.-C.; Yin, G.-W.; Ye, F.; Xu, Z.; Xu, L.-W. Angew. Chem. Int. Ed. 2020, 59, 790.
(d) Shi, M.; Shao, L.-X.; Lu, J.-M.; Wei, Y.; Mizuno, K.; Maeda, H. Chem. Rev. 2010, 110, 5883.
(e) Zhao, Z.-Y.; Nie, Y.-X.; Tang, R.-H.; Yin, G.-W.; Cao, J.; Xu, Z.; Cui, Y.-M.; Zheng, Z.-J.; Xu, L.-W. ACS catal. 2019, 9, 9110.
[25] (a) Rettenmeier, E.; Schuster, A. M.; Rudolph, M.; Rominger, F.; Gade, C. A.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2013, 52, 5880.
(b) Geng, W.; Wang, C.; Guang, J.; Hao, W.; Zhang, W.-X.; Xi, Z. Chem. Eur. J. 2013, 19, 8657.
(c) Ye, J.; Huang, X.; Wang, X.; Zheng, T.; Gao, Y.; Gong, W.; Ning, G. Chin. J. Org. Chem. 2016, 36, 1299(in Chinese). (叶俊伟, 黄雪明, 王潇潇, 郑婷, 高远, 贡卫涛, 宁桂玲, 有机化学, 2016, 36, 1299.)
[26] (a) Yang, C.; Cho, S.; Chiechi, R. C.; Walker, W.; Coates, N. E.; Moses, D.; Heeger, A. J.; Wudl, F. J. Am. Chem. Soc. 2008, 130, 16524.
(b) Süss-Fink, G. Dalton Trans. 2010, 39, 1673.
(c) Kim, H.; Choi, T.; Cha, M. C.; Chang, J. Y. J. Polym. Sci., Part A:Polym. Chem. 2013, 51, 3646.
(d) Chen, Z.; Mao, Y.; Cao, Y.; Liang, S.; Song, S.; Ni, C.; Liu, Z.; Ye, X.; Shen, A.; Zhu, H. Chin. J. Org. Chem. 2018, 38, 2937(in Chinese). (陈志康, 毛远洪, 曹育才, 梁胜彪, 宋莎, 倪晨, 刘振宇, 叶晓峰, 沈安, 朱红平, 有机化学, 2018, 36, 2937.)
[27] (a) Jiang, X.; Wang, R. Chem. Rev. 2013, 113, 5515.
(b) Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359.
(c) Liu, W.; Wu, Y.; Li, L.; Li, X. Chin. J. Org. Chem. 2016, 36, 1501(in Chinese). (刘文香, 吴宇强, 李灵芝, 李霞, 有机化学, 2016, 36, 1501.)
[28] (a) Funami, H.; Kusama, H.; Iwasawa, N. Angew. Chem. Int. Ed. 2007, 46, 909.
(b) Lee, J. H.; Toste, F. D. Angew. Chem. Int. Ed. 2007, 46, 912.
(c) Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottländer, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem. Int. Ed. 2011, 50, 5090.
[29] (a) Li, H.; Zhang, W.-X.; Xi, Z. Chem. Eur. J. 2013, 19, 12859.
(b) Xi, Z. F.; Li, P. X. Angew. Chem. Int. Ed. 2000, 39, 2950.
(c) Xi, Z. F.; Song, Q. L.; Chen, J. L.; Guan, H. R.; Li, P. X. Angew. Chem. Int. Ed. 2001, 40, 1913.
[30] Cheng, X.; Zhu, L.; Lin, M.; Chen, J.; Huang, X. Chem. Commun. 2017, 53, 3745.
[31] Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612.
[32] (a) Xu, M.; Wang, Y.; Yang, F.; Wu, C.; Wang, Z.; Ye, B.; Jiang, X.; Zhao, Q.; Li, J.; Liu, Y.; Zhang, J.; Tian, G.; He, Y.; Shen, J.; Jiang, H. Eur. J. Med. Chem. 2018, 145, 74.
(b) Ravi Ganesh, K.; Pachore, S. S.; Pratap, T. V.; Umesh, K.; Basaveswara Rao, M. V.; Murthy, C.; Suresh Babu, M. Synth. Commun. 2015, 45, 2676.
[33] (a) Shi, M.; Lu, J.-M.; Wei, Y.; Shao, L.-X. Acc. Chem. Res. 2012, 45, 641.
(b) Zhang, D.-H.; Tang, X.-Y.; Shi, M. Acc. Chem. Res. 2014, 47, 913.
[34] Yamago, S.; Nakamura, E. Org. React. (Hoboken, NJ, U. S.), 2002, 61, 15.
[35] (a) Shen, X.-Y.; Peng, X.-S.; Wong, H. N. C. Org. Lett. 2016, 18, 1032.
(b) Lu, X.-L.; Lyu, M.-Y.; Peng, X.-S.; Wong, H. N. C. Angew. Chem. Int. Ed. 2018, 57, 11365.
[36] Gibson, S. E.; Mainolfi, N. Angew. Chem. Int. Ed. 2005, 44, 3022.
[37] Rios-Gutierrez, M.; Domingo, L. R. Eur. J. Org. Chem. 2019, 2019, 267.
[38] Zhou, Y.-Y.; Uyeda, C. Science 2019, 363, 857.
[39] (a) Binger, P.; Wedemann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 1998, 113.
(b) Binger, P.; Brinkmann, A.; Wedemann, P. Chem. Ber. Recl. 1983, 116, 2920.
(c) Binger, P.; McMeekin, J. Angew. Chem. Int. Ed. 1974, 13, 466.
(d) Binger, P.; McMeekin, J. Angew. Chem. Int. Ed. 1973, 12, 995.
(e) Ohta, T.; Takaya, H.; Trost, B. M.; Fleming, I.; Paquette, L. A. Metal-catalyzed Cycloaddition of Small Ring Compounds, Petgamon, Oxford, 1991, p. 1185.
[40] Fu, N.-Y.; Chan, S.-H.; Wong, H. N. C. In The Chemistry of Cyclobutanes, 1 ed.; Eds.:Rappoport, Z., Liebman, J. F., John Wiley & Sons, Ltd., Chichester, 2005, p. 357.
[41] (a) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry, Vol. 21, Eds.:Gribble, G. W.; Joule, J. A., Elsevier, Oxford, UK, 2009, p. 179.
(b) Hou X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry, Vol. 13, Eds.:Gribble, G. W.; Gilchrist, T. L., Elsevier, Oxford, UK, 2001, p. 130.
(c) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
[42] Chen, F.; Chen, K.; Zhang, Y.; He, Y.; Wang, Y.-M.; Zhu, S. J. Am. Chem. Soc. 2017, 139, 13929.
[43] (a) Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285.
(b) Lanke, V.; Zhang, F.-G.; Kaushansky, A.; Marek, I. Chem. Sci. 2019, 10, 9548.
[44] O'Connor, A. R.; Urbin, S. A.; Moorhouse, R. A.; White, P. S.; Brookhart, M. Organometallics 2009, 28, 2372.
[45] Minami, A.; Ozaki, T.; Liu, C.; Oikawa, H. Nat. Prod. Rep. 2018, 35, 1330.
[46] Yang, Y.-L.; Li, W.; Wang, H.; Yang, L.; Yuan, J.-Z.; Cai, C.-H.; Chen, H.-Q.; Dong, W.-H.; Ding, X.-P.; Jiang, B.; Mándi, A.; Kurtán, T.; Mei, W.-L.; Dai, H.-F. Fitoterapia 2019, 138.
[47] Krawczyk, A. R.; Jones, J. B. J. Org. Chem. 1989, 54, 1795.
[48] (a) Lin, F.; Peng, H.-Y.; Chen, J.-X.; Chik, D. T. W.; Cai, Z.; Wong, K. M. C.; Yam, V. W. W.; Wong, H. N. C. J. Am. Chem. Soc. 2010, 132, 16383.
(b) Wu, A.-H.; Hau, C.-K.; Wong, H. N. C. Adv. Synth. Catal. 2007, 349, 601.
(c) Peng, H.-Y.; Lam, C.-K.; Mak, T. C. W.; Cai, Z.; Ma, W.-T.; Li, Y.-X.; Wong, H. N. C. J. Am. Chem. Soc. 2005, 127, 9603.
[49] Jackson, D. A.; Lacy, P. H.; Smith, D. C. C. J. Chem. Soc., Perkin Trans. 1 1989, 215.
[50] Gonzalez, M. J.; Gonzalez, J.; Vicente, R. Eur. J. Org. Chem. 2012, 2012, 6140.
[51] (a) Meinwald, J.; Labana, S. S.; Chadha, M. S. J. Am. Chem. Soc. 1963, 85, 582.
(b) House, H. O. J. Am. Chem. Soc. 1955, 77, 3070.
[52] Ma, D.; Miao, C.-B.; Sun, J. J. Am. Chem. Soc. 2019, 141, 13783.
[53] Chang, M.-Y.; Lin, C.-H. J. Chin. Chem. Soc. (Taipei, Taiwan) 2011, 58, 853.
[54] Chang, M.-Y.; Lee, N.-C.; Lee, M.-F.; Huang, Y.-P.; Lin, C.-H. Tetrahedron Lett. 2010, 51, 5900.
[55] Duan, J. J. W.; Lu, Z.; Jiang, B.; Yang, B. V.; Doweyko, L. M.; Nirschl, D. S.; Haque, L. E.; Lin, S.; Brown, G.; Hynes, J.; Tokarski, J. S.; Sack, J. S.; Khan, J.; Lippy, J. S.; Zhang, R. F.; Pitt, S.; Shen, G.; Pitts, W. J.; Carter, P. H.; Barrish, J. C.; Nadler, S. G.; Salter-Cid, L. M.; McKinnon, M.; Fura, A.; Schieven, G. L.; Wrobleski, S. T. Biorg. Med. Chem. Lett. 2014, 24, 5721.
[56] Chang, M. Y.; Lee, N. C.; Lee, M. F.; Huang, Y. P.; Lin, C. H. Tetrahedron Lett. 2010, 51, 5900.
Options
文章导航

/

〈 〉