以二氧化碳为C1合成子的羧基化/环化反应研究进展

doi:10.6023/cjoc202003039

摘要/Abstract

二氧化碳具有价廉易得、储量丰富及无毒等优点，在有机合成反应中是一种理想的C1合成子.近年来，以二氧化碳作为羰基/羧基源，通过环化反应，特别是多组分环化反应构建含羰基杂环化合物，已经取得了重要的研究进展.主要总结了利用含氮、氧亲核原子的试剂与常压条件下二氧化碳的环化反应构建苯并噁嗪、环碳酸酯、内酰胺、2，4-二噁唑啉酮等含羰基杂环结构的工作；其次，也总结了利用含碳亲核原子的试剂与二氧化碳羧基化反应的相关工作.

关键词: 二氧化碳, 多组分反应, 环化反应, 羧酸, 杂环化合物

Carbon dioxide is a readily available, low-cost, abundant, non-toxic C1 source, which can potentially serve as an ideal building block in synthetic chemistry. Recently, much progress, expecially multi-component reactions (MCRs) has been achieved in construction of carbonyl-containing heterocycles through annulation by using carbon dioxide as carbonyl/carboxyl source. Herein, the advances on the annulation reaction of atmospheric CO₂ with N-, and O-nucleophiles for the constructioin of various carbonyl-containing heterocycles, including benzoxazin, cyclic carbamates, lactams, oxazolidine-2,4-diones are reviewed. In addition, the carboxylation of C-nucleophiles with CO₂ toward carboxylic acids is also summarized.

Key words: carbon dioxide, multicomponent reaction, annulation, carboxylic acid, heterocycle

引用此文

周聪, 李渺, 于金涛, 孙松, 成江. 以二氧化碳为C1合成子的羧基化/环化反应研究进展[J]. 有机化学, 2020, 40(8): 2221-2231.

Zhou Cong, Li Miao, Yu Jintao, Sun Song, Cheng Jiang. Recent Progress in the Carboxylation/Cyclization Reactions Using Carbon Dioxide as the C1 Source[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2221-2231.

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参考文献

[1] Le Quere, C.; Andrew, R. M.; Friedlingstein, P.; Sitch, S.; Hauck, J.; Pongratz, J.; Pickers, P. A.; Korsbakken, J. I.; Peters, G. P.; Canadell, J. G.; Arneth, A.; Arora, V. K.; Barbero, L.; Bastos, A.; Bopp, L.; Chevallier, F.; Chini, L. P.; Ciais, P.; Doney, S. C.; Gkritzalis, T.; Goll, D. S.; Harris, I.; Haverd, V.; Hoffman, F. M.; Hoppema, M.; Houghton, R. A.; Hurtt, G.; Ilyina, T.; Jain, A. K.; Johannessen, T.; Jones, C. D.; Kato, E.; Keeling, R. F.; Goldewijk, K. K.; Landschutzer, P.; Lefevre, N.; Lienert, S.; Liu, Z.; Lombardozzi, D.; Metzl, N.; Munro, D. R.; Nabel, J. E. M. S.; Nakaoka, S.; Neill, C.; Olsen, A.; Ono, T.; Patra, P.; Peregon, A.; Peters, W.; Peylin, P.; Pfeil, B.; Pierrot, D.; Poulter, B.; Rehder, G.; Resplandy, L.; Robertson, E.; Rocher, M.; Rodenbeck, C.; Schuster, U.; Schwinger, J.; Seferian, R.; Skjelvan, I.; Steinhoff, T.; Sutton, A.; Tans, P. P.; Tian, H. Q.; Tilbrook, B.; Tubiello, F. N.; van der Laan-Luijkx, I. T.; van der Werf, G. R.; Viovy, N.; Walker, A. P.; Wiltshire, A. J.; Wright, R.; Zaehle, S.; Zheng, B. Earth Syst. Sci. 2018, 10, 2141.
[2] (a) Hulla, M.; Dyson, P. J. Angew. Chem., Int. Ed. 2020, 59, 1002.
(b) Yeung, C. S. Angew. Chem., Int. Ed. 2019, 58, 5492.
(c) Luo, J.; Larrosa, I. ChemSusChem 2017, 10, 3317.
(d) Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337.
(e) Lu, X. Carbon Dioxide and Organometallics, Springer International Publishing, Switzerland, 2016.
(f) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
(g) Bhanage, B. M.; Arai, M. Transformation and Utilization of Carbon Dioxide, Springer-Verlag, Berlin, Heidelberg, 2014.
(h) Zhang, L.; Hou, Z. Chem. Sci. 2013, 4, 3395.
(i) Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510.
(j) Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435.
(k) Aresta, M. Carbon Dioxide as Chemical Feedstock, Wiley-VCH, Weinheim, 2010.
(l) Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
[3] (a) Aresta, M.; Dibenedetto, A.; Angelini, A. Chem. Rev. 2014, 114, 1709.
(b) Hua, B.; Guild, C.; Suib, S. L. J. CO₂ Util. 2013, 1, 18.
[4] (a) Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S. G. Chem.-Eur. J. 2012, 18, 5460.
(b) Weibel, J.-M.; Blanc, A.; Pale, P. Chem. Rev. 2008, 108, 3149.
[5] (a) Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkovc, A. A.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861.
(b) Liu, X.; He, L.-N. Top. Curr. Chem. 2017, 375, 21.
(c) Zhang, Z.; Ju, T.; Ye, J.-H.; Yu, D.-G. Synlett 2017, 28, 741.
(d) Sekine, K.; Yamada, T. Chem. Soc. Rev. 2016, 45, 4524.
[6] Wu, L.; Liu, Q.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 6310.
[7] (a) Guo, C.-X.; Zhang, W.-Z.; Zhang, N.; Lu, X.-B. J. Org. Chem. 2017, 82, 7637.
(b) Zhang, W.-Z.; Yang, M.-W.; Lu, X.-B. Green Chem. 2016, 18, 4181.
(c) Zhang, W.-Z.; Yang, M.-W.; Yang, X.-T.; Shi, L.-L. Wang, H.-B.; Lu, X.-B. Org. Chem. Front. 2016, 3, 217.
(d) Zhang, W.-Z.; Xia, T.; Yang, X.-T.; Lu, X.-B. Chem. Commun. 2015, 51, 6175.
(e) Wang, Y.-B.; Wang, Y.-M.; Zhang, W.-Z.; Lu, X.-B. J. Am. Chem. Soc. 2013, 135, 11996.
[8] (a) Lang, X.-D.; You, F.; He, X.; Yu, Y.-C.; He, L.-N. Green Chem. 2019, 21, 509.
(b) He, X.; Yao, X.-Y.; Chen, K.-H.; He, L.-N. ChemSusChem 2019, 12, 5081.
(c) Lang, X.-D.; You, F.; He, X.; Yu, Y.-C.; He, L.-N. Green Chem. 2019, 21, 509.
(d) Wang, M.-Y.; Cao, Y.; Liu, X.; Wang, N.; He, L.-N.; Li, S.-H. Green Chem. 2017, 19, 1240.
(e) Wang, M.-Y.; Song, Q.-W.; Ma, R.; Xie, J.-N.; He, L.-N. Green Chem. 2016, 18, 282.
(f) Xie, J.-N.; Yu, B.; Guo, C.-X.; He, L.-N. Green Chem. 2015, 17, 4061.
[9] (a) Ouyang, L.; Tang, X.; He, H.; Qi, C.; Xiong, W.; Ren, Y.; Jiang, H. Adv. Synth. Catal. 2015, 357, 2556.
(b) Qi, C.; Jiang, H.; Huang, L.; Yuan, G.; Ren, Y. Org. Lett. 2013, 13, 5520.
(c) Zhao, J.; Huang, H.; Qi, C.; Jiang, H. Eur. J. Org. Chem. 2012, 5665.
[10] (a) Hu, J.; Ma, J.; Zhu, Q.; Zhang, Z.; Wu, C.; Han, B. Angew. Chem., Int. Ed. 2015, 54, 5399.
(b) Gao, X.; Yu, B.; Yang, Z.; Zhao, Y.; Zhang, H.; Hao, L.; Han, B.; Liu, Z. ACS Catal. 2015, 5, 6648.
[11] (a) Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2016, 55, 10022.
(b) Song, L.; Zhu, L.; Zhang, Z.; Ye, J.-H.; Yan, S.-S.; Han, J.-L.; Yin, Z.-B.; Lan, Y.; Yu, D.-G.; Org. Lett. 2018, 20, 3776.
(c) Zhang, Z.; Ju, T.; Miao, M.; Han, J.-L.; Zhang, Y.-H.; Zhu, X.-Y.; Ye, J.-H.; Yu, D.-G.; Zhi, Y.-G. Org. Lett. 2017, 19, 396.
(d) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G. Org. Lett. 2018, 20, 3049.
[12] (a) Sadamitsu, Y.; Komatsuki, K.; Saito, K.; Yamada, T. Org. Lett. 2017, 19, 3191.
(b) Ishida, T.; Kikuchi, S.; Tsubo, T.; Yamada, T. Org. Lett. 2013, 15, 848.
(c) Ishida, T.; Kikuchi, S.; Yamada, T. Org. Lett. 2013, 15, 3710.
(d) Kikuchi, S.; Sekine, K.; Ishida, T.; Yamada, T. Angew. Chem., Int. Ed. 2012, 51, 6989.
[13] (a) Wang, S.; Xi, C. Chem. Soc. Rev. 2019, 48, 382.
(b) Wang, L.; Sun, W.; Liu, C. Chin. J. Chem. 2018, 36, 353.
(c) Zhang, W.; Zhang, N.; Guo, C.; Lu, X.-B. Chin. J. Org. Chem. 2017, 37, 1309(in Chinese). (张文珍, 张宁, 郭春晓, 吕小兵, 有机化学, 2017, 37, 1309.)
(d) Zhu, Q.; Wang, L.; Xia, C.; Liu, C. Chin. J. Org. Chem. 2016, 36, 2813(in Chinese). (朱庆, 王露, 夏春谷, 刘超, 有机化学, 2016, 36, 2813.)
(e) Rintjema, J.; Kleij, A. W. Synthesis 2016, 48, 3863.
(f) Yu, B.; He, L.-N. ChemSusChem 2015, 8, 52.
(g) Kielland, N.; Whiteoak, C.; Kleij, A. W. Adv. Synth. Catal. 2013, 355, 2115.
(h) Lu, X.-B.; Darensbourg, D. Chem. Soc. Rev. 2012, 41, 1462.
[14] (a) Miyashiro, J.; Woods, K. W.; Park, C. H.; Liu, X.; Shi, Y.; Johnson, E. F.; Bouska, J. J.; Olson, A. M.; Luo, Y.; Fry, E. H.; Giranda, V. L.; Penning, T. D. Bioorg. Med. Chem. Lett. 2009, 19, 4050.
(b) Angibaud, P. R.; Venet, M. G.; Filliers, W.; Broeckx, R.; Ligny, Y. A.; Muller, P.; Poncelet, V. S.; End, D. W. Eur. J. Org. Chem. 2004, 479.
[15] (a) Ferguson, M J.; Zeng, F.; Alwis, N.; Alper, H. Org. Lett. 2013, 15, 1998.
(b) Liang, Z.; Zhang, J.; Liu, Z.; Wang, K.; Zhang, Y. Tetrahedron 2013, 69, 6519.
[16] (a) Zhang, Z.; Liao, L.-L.; Yan, S.-S.; Wang, L.; He, Y.-Q.; Ye, J.-H.; Li, J.; Zhi, Y.-G.; Yu, D.-G. Angew. Chem., Int. Ed. 2016, 55, 7068.
(b) Wang, S.; Shao, P.; Du, G.; Xi, C. J. Org. Chem. 2016, 81, 6672.
[17] Sun, S.; Hu, W.-M.; Gu, N.; Cheng, J. Chem.-Eur. J. 2016, 22, 18729.
[18] (a) Ishida, T.; Kikuchi, S.; Tsubo, T.; Yamada, T. Org. Lett. 2013, 15, 848.
(b) Childers, W. E. Jr.; Baudy, R. B. J. Med. Chem. 2007, 50, 2557.
[19] Wang, B.; Sun, S.; Yu, J.-T.; Jiang, Y.; Cheng, J. Org. Lett. 2017, 19, 4319.
[20] (a) Pastore, V.; Sabatier, L.; Enrique, A.; Marder, M.; Bruno-Blanch, L. E. Bioorg. Med. Chem. 2013, 21, 841.
(b) Heerding, D. A.; Christmann, L. T.; Clark, T. J.; Holmes, D. J.; Rittenhouse, S. F.; Takata, D. T.; Venslavsky, J. W. Bioorg. Med. Chem. Lett. 2003, 13, 3771.
[21] (a) Zhou, H.; Mu, S.; Ren, B.-H.; Zhang, R.; Lu, X.-B. Green Chem. 2019, 21, 991.
(b) Chen, G.; Fu, C.; Ma, S. Org. Biomol. Chem. 2011, 9, 105.
[22] Zhou, C.; Dong, Y.; Yu, J.-T.; Sun, S.; Cheng, J. Chem. Commun. 2019, 55, 13685.
[23] (a) Yin, Z.; Ye, J.; Zhou, W.; Zhang, Y.; Ding, L.; Gui, Y.; Yan, S.; Li, J.; Yu, D. Org. Lett. 2018, 20, 190.
(b) Sun, L.; Ye, J.; Zhou, W.; Zeng, X.; Yu, D. Org. Lett. 2018, 20, 3049.
[24] (a) Commons, T. J.; Jenkins, D. J.; Trybulski, E. J.; Fensome, A. US 20090197878, 2009.
(b) Collins, M. A.; Hudak, V.; Bender, R.; Fensome, A.; Zhang, P.; Miller, L.; Winneker, R. C.; Zhang, Z.; Zhu, Y.; Cohen, J. Bioorg. Med. Chem. Lett. 2004, 14, 2185.
[25] (a) Zhao, Y.; Huang, B.; Yang, C.; Chen, Q.; Xia, W. Org. Lett. 2016, 18, 5572.
(b) Hernandez, E.; Velez, J. M.; Vlaar, C. P. Tetrahedron Lett. 2007, 48, 8972.
(c) Lagu, B.; Pio, B.; Lebedev, R.; Yang, M.; Pelton, P. D. Bioorg. Med. Chem. Lett. 2007, 17, 3497.
[26] Sun, S.; Zhou, C.; Dong, Y.; Yu, J.-T.; Cheng, J. Org. Lett. 2019, 21, 6579.
[27] Xiong, H.; Wu, X.; Wang, H.; Sun, S.; Yu, J.; Cheng, J. Adv. Synth. Catal. 2019, 361, 3538.
[28] Frantz, M.-C.; Rodrigo, J.; Boudier, L.; Durroux, T.; Mouillac, B.; Hibert, M. J. Med. Chem. 2010, 53, 1546.
(b) Collins, M. A.; Hudak, V.; Bender, R.; Fensome, A.; Zhang, P.; Miller, L.; Winneker, R. C.; Zhang, Z.; Zhu, Y.; Cohen, J. Bioorg. Med. Chem. Lett. 2004, 14, 2185.
[29] Xia, M.; Hu, W.; Sun, S.; Yu, J.-T.; Cheng, J. Org. Biomol. Chem. 2017, 15, 4064.
[30] (a) Holtwick, J. B.; Leonard, N. J. J. Org. Chem. 1981, 46, 3681.
(b) Holtwick, J. B.; Golankiewicz, B.; Holmes, B. N.; Leonard, N. J. J. Org. Chem. 1979, 44, 3835.
[31] (a) Kahveci, B.; Yilmaz, F.; Mentese, E.; Ulker, S. Chem. Heterocycl. Compd. 2015, 51, 447.
(b) Han, S.; Zhang, F.-F.; Xie, X.; Chen, J.-Z. Eur. J. Med. Chem. 2014, 74, 73.
[32] Wu, X.; Sun, S.; Wang, B.; Cheng, J. Adv. Synth. Catal. 2017, 359, 3855.
[33] Ren, X.; Zheng, Z.; Zhang, L.; Wang, Z.; Xia, C.; Ding, K. Angew. Chem., Int. Ed. 2017, 56, 310.
[34] Kane, J. M.; Baron, B. M.; Dudley, M. W.; Sorensen, S. M.; Staeger, M. A.; Miller, F. P. J. Med. Chem. 1990, 33, 2772.
[35] (a) Sharma, M. C.; Sharma, S.; Sharma, P.; Kumar, A.; Bhadoriya, K. S. Med. Chem. Res. 2014, 23, 2486.
(b) Pai, N. R.; Dubhashi, D. S.; Pusalkar, D. A. Int. J. Pharm. Sci. Rev. Res. 2010, 4, 180.
[36] (a) Song, Q.-W.; Yu, B.; Li, X.-D.; Ma, R.; Diao, Z.-F.; Li, R.-G.; Li, W.; He, L.-N. Green Chem. 2014, 16, 1633.
(b) Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072.
(c) Kayaki, Y.; Yamamoto, M.; Ikariya, T. Angew. Chem., Int. Ed. 2009, 48, 419.
(d) Jiang, H.-F.; Wang, A.-Z.; Liu, H.-L.; Qi, C.-R. Eur. J. Org. Chem. 2008, 2309.
[37] (a) Sun, S.; Wang, B.; Gu, N.; Yu, J.-T.; Cheng, J. Org. Lett. 2017, 19, 1088.
(b) Iritani, K.; Yanagihara, N.; Utimoto, K. J. Org. Chem. 1986, 51, 5499.
[38] (a) León, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221.
(b) Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936.
[39] Sun, S.; Yu, J.-T.; Jiang, Y.; Cheng, J. Adv. Synth. Catal. 2015, 357, 2022.
[40] (a) Windsor, M. A.; Hermanson, D. J.; Kingsley, P. J.; Xu, S.; Crews, B. C.; Ho, W.; Keenan, C. M.; Banerjee, S.; Sharkey, K. A.; Marnett, L. J. ACS Med. Chem. Lett. 2012, 3, 759.
(b) Zhu, S.-F.; Yu, Y.-B.; Li, S.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2012, 51, 8872.
(c) Hu, W.; Chen, C.-C.; Xue, G.; Chan, A. S. C. Tetrahedron:Asymmetry 1998, 9, 4183.
[41] Stemke, J. E.; Chamberlin, A. R.; Bond, F. T. Tetrahedron Lett. 1976, 17, 2947.
[42] Sun, S.; Yu, J.-T.; Jiang, Y.; Cheng, J. J. Org. Chem. 2015, 80, 2855.