不对称催化实现的二氧化碳固定直接合成光学活性小分子的最新进展

doi:10.6023/cjoc202002032

有机化学 ›› 2020, Vol. 40 ›› Issue (8): 2208-2220.DOI: 10.6023/cjoc202002032 上一篇下一篇

所属专题：二氧化碳虚拟合辑

综述与进展

不对称催化实现的二氧化碳固定直接合成光学活性小分子的最新进展

郭霄^a, 王亚洲^b, 陈洁^b, 李公强^a, 夏纪宝^b

a 南京工业大学先进材料研究院柔性电子重点实验室江苏省国家先进材料协同创新中心南京 211816;
b 中国科学院兰州化学物理研究所中国科学院兰州化学物理研究所苏州研究院羰基合成与选择氧化国家重点实验室分子合成科学卓越创新中心兰州 730000

收稿日期:2020-02-24 修回日期:2020-05-08 发布日期:2020-05-15
通讯作者: 陈洁, 李公强, 夏纪宝 E-mail:chenjie318827@hotmail.com;iamgqli@njtech.edu.cn;jibaoxia@licp.cas.cn
基金资助:
国家自然科学基金（Nos.21702212，21772208）和中国科学院前沿科学基金（No.QYZDJSSW-SLH051）资助项目.

Recent Advances of CO₂ Fixation via Asymmetric Catalysis for the Direct Synthesis of Optically Active Small Molecules

Guo Xiao^a, Wang Yazhou^b, Chen Jie^b, Li Gongqiang^a, Xia Ji-Bao^b

a Key Laboratory of Flexible Electronic&Institute of Advanced Materials, Jiangsu National Synergistic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics(LICP), Chinese Academy of Sciences, Lanzhou 730000

Received:2020-02-24 Revised:2020-05-08 Published:2020-05-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21702212, 21772208) and the Key Research Program of Frontier Sciences of Chinese Academy of Sciences (No. QYZDJSSW-SLH051).

文章分享

摘要/Abstract

固定二氧化碳（CO₂）的工业过程远远落后于人类活动产生的碳排放量.由于二氧化碳是一种丰富、无毒且廉价易得的碳资源，因此开发出将二氧化碳转化为有价值的产品，以实现可持续发展的化学合成是非常有意义的.基于过渡金属催化和有机催化活化CO₂的机理研究，近年来已开发出多种有效的CO₂的不对称化学固定方法.讨论了通过CO₂的不对称化学固定实现的小分子化合物的手性合成的进展.通过阐述催化剂、CO₂和底物之间的相互作用，旨在激发CO₂不对称转化的新型催化系统的设计.

关键词: 二氧化碳, 不对称催化, 对映选择性, 羧基化, 环化反应

Industrial processes of fixing carbon dioxide (CO₂) lag far behind the carbon emission generated by human activity. Since CO₂ is an abundant, non-toxic, and cost-effective one carbon source, it is highly desirable to develop methodologies on converting CO₂ into valuable products for sustainable purpose. Based on the mechanistic insight of CO₂ activation by transition-metal catalyst and organocatalyst, a variety of efficient asymmetric CO₂ chemical fixation processes have been developed in recent years. This review discusses the advances of enantioselective synthesis of small molecules by asymmetric catalytic reactions with CO₂. The interaction between catalyst, CO₂ and substrate has been elaborated aiming to inspire the design of new catalytic systems for asymmetric CO₂ transformation.

Key words: carbon dioxide, asymmetric catalysis, enantioselectivity, carboxylation, cyclization

引用此文

郭霄, 王亚洲, 陈洁, 李公强, 夏纪宝. 不对称催化实现的二氧化碳固定直接合成光学活性小分子的最新进展[J]. 有机化学, 2020, 40(8): 2208-2220.

Guo Xiao, Wang Yazhou, Chen Jie, Li Gongqiang, Xia Ji-Bao. Recent Advances of CO₂ Fixation via Asymmetric Catalysis for the Direct Synthesis of Optically Active Small Molecules[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2208-2220.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Scott, A. Chem. Eng. News 2015, 93, 10.
[2] Aresta, M. Carbon Dioxide as Chemical Feedstock, Wiley-VCH, Weinheim, 2010.
[3] Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nat. Commun. 2015, 6, 5933.
[4] Fiorani, G.; Guo, W.; Kleij, A.-W. Green Chem. 2015, 17, 1375.
[5] Yu, B.; He, L.-N. ChemSusChem 2015, 8, 52.
[6] Maeda, C.; Miyazaki, Y.; Ema, T. Catal. Sci. Technol. 2014, 4, 1482.
[7] Tlili, A.; Frogneux, X.; Blondiaux, E.; Cantat, T. Angew. Chem., Int. Ed. 2014, 53, 2543.
[8] Yuan, G.; Qi, C.; Wu, W.; Jiang, H. Curr. Opin. Green Sust. Chem. 2017, 3, 22.
[9] Zhang, W.; Zhang, N.; Guo, C.-X.; Lü, X. 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.)
[10] Zhang, Z.; Ju, T.; Ye, J.-H.; Yu, D.-G. Synlett 2017, 28, 741.
[11] Gui, Y.-Y.; Zhou, W.-J.; Ye, J.-H.; Yu, D.-G. ChemSusChem 2017, 10, 1337.
[12] Cao, Y.; He, X.; Wang, N.; Li, H.-R.; He, L.-N. Chin. J. Chem. 2018, 36, 644.
[13] Zhao, Y., Liu, Z.-M. Chin. J. Chem. 2018, 36, 455
[14] Hu, J.; Liu, H.; Han, B. Sci. China Chem. 2018, 61, 1486.
[15] Tan, F.; Yin, G. Chin. J. Chem. 2018, 36, 545.
[16] Zhang, Z.; Gong, L.; Zhou, X.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Acta Chim. Sinica 2019, 77, 783(in Chinese). (张振, 龚莉, 周晓渝, 颜思顺, 李静, 余达刚, 化学学报, 2019, 77, 783.)
[17] Cheng, L.; Xie, J.-H. Chin. J. Org. Chem. 2020, 40, 247(in Chinese). (程磊, 谢建华, 有机化学, 2020, 40, 247.)
[18] Kolbe, H. Justus Liebigs Ann. Chem. 1860, 113,125.
[19] Lindsey, A.-S.; Jeskey, H. Chem. Rev. 1957, 57, 583.
[20] Luo, J.; Preciado, S.; Xia, P.; Larrosa, L. Chem.-Eur. J. 2016, 22, 6798.
[21] Zhang, W.-Z.; Li, H.; Zeng, Y.; Tao, X.; Lu, X. Chin. J. Chem. 2018, 36, 112.
[22] Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
[23] White, J.-L.; Baruch, M.-F.; Pander III, J.-E.; Hu, Y.-I.; Fortmeyer, C.; Park, J.-E.; Zhang, T.; Liao, K.; Gu, J.; Yan, Y.; Shaw, T.-W.; Abelev, E.; Bocarsly, A.-B. Chem. Rev. 2015, 115, 12888.
[24] Wang, J.-L.; Miao, C.-X.; Dou, X.-Y.; Gao, J.; He, L.-N. Curr. Org. Chem. 2011, 15, 621.
[25] Tlili, A.; Blondiaux, E.; Frogneux, X.; Cantat, T. Green Chem. 2015, 17, 157.
[26] Li, Y.; Cui, X.; Dong, K.; Junge, K.; Beller, M. ACS Catal. 2017, 7, 1077.
[27] Liu, M.; Qin, T.; Zhang, Q.; Fang, C.; Fu, Y.; Lin, B.-L. Sci. China Chem. 2015, 58, 1524.
[28] Zhang, L.; Zhao, Z.-J.; Gong, J. Angew. Chem., Int. Ed. 2017, 56, 11326.
[29] Yu, D.; Teong, S.-P.; Zhang, Y. Coord. Chem. Rev. 2015, 293-294, 279.
[30] Liu, A.-H.; Yu, B.; He, L.-N. Greenhouse Gas Sci. Technol. 2015, 5, 17.
[31] Yeung, C.-S.; Dong, V.-M.; Top. Catal. 2014, 57, 1342.
[32] Zhang, W.; Lu, X. Chin. J. Catal. 2012, 33, 745.
[33] Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956.
[34] Ackermann, L. Angew. Chem., Int. Ed,.2011, 50, 3842.
[35] Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435.
[36] Börjesson, M.; Moragas, T.; Gallego, D.; Martin, R. ACS Catal. 2016, 6, 6739.
[37] Chen, Y.-G.; Xu, X.-T.; Zhang, K.; Li, Y.-Q.; Zhang, L.-P.; Fang, P.; Mei,T.-S. Synthesis 2018, 50, 35.
[38] Riduan, S.-N.; Zhang, Y.; Ying, J.-Y. Angew. Chem., Int. Ed. 2009, 48, 3322.
[39] Gomes, C.-D.-N.; Jacquet, O.; Villiers, C.; Thuery, P.; Ephritikhine, M.; Cantat, T. Angew. Chem., Int. Ed. 2012, 51, 187.
[40] Xin, Z.; Lescot, C.; Friis, S. D.; Daasbjerg, K.; Skrydstrup, T. Angew. Chem., Int. Ed. 2015, 54, 6862.
[41] Kielland, N.; Whiteoak, C.-J.; Kleij, A.-W. Adv. Synth. Catal. 2013, 355, 2115.
[42] Lu, X.-B.; Darensbourg, D.-J. Chem. Soc. Rev. 2012, 41, 1462.
[43] Decortes, A.; Castilla, A.-M.; Kleij, A.-W. Angew. Chem., Int. Ed. 2010, 49, 9822.
[44] Vaitla, J.; Guttormsen, Y.; Mannisto, J.-K.; Nova, A.; Repo, T.; Bayer A.; Hopmann, K.-H. ACS Catal. 2017, 7, 7231.
[45] Sato, F.; Iijima, S.; Sato, M. J. Chem. Soc., Chem. Commun. 1981, 180.
[46] Beng, T.-K.; Gawley, R.-E. J. Am. Chem. Soc. 2010, 132, 12216.
[47] Perrona, Q.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 2611.
[48] Egami, H.; Sato, K.; Asada, J.; Kawato, Y.; Hamashima, Y.; Tetrahedron 2015, 71, 6384.
[49] Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2002, 124, 10008
[50] Takimoto, M.; Nakamura, Y.; Kimura, K.; Mori, M. J. Am. Chem. Soc. 2004, 126, 5956.
[51] Ishii, M.; Mori, F.; Tanaka, K. Chem.-Eur. J. 2014, 20, 2169.
[52] Williams, C.-M.; Johnson, J.-B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936.
[53] Greenhalgh, M.-D.; Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900.
[54] Hayashi, C.; Hayashi, T.; Kikuchi, S.; Yamada, T. Chem. Lett. 2014, 43, 565.
[55] Hayashi, C.; Hayashi, T.; Yamada, T. Bull. Chem. Soc. Jpn. 2015, 88, 862.
[56] Kawashima, S.; Aikawa, K.; Mikami, K.;Eur. J. Org. Chem. 2016, 19, 3166.
[57] Dian, L.; Müller, D.-S.; Marek, I. Angew. Chem., Int. Ed. 2017, 56, 6783.
[58] Gui, Y.-Y.; Hu, N.; Chen, X.-W.; Liao, L.-L.; Ju, T.; Ye, J.-H.; Zhang, Z.; Li, J.; Yu, D.-G. J. Am. Chem. Soc. 2017, 139, 17011.
[59] Chen, X.-W.; Zhu, L.; Gui, Y.-Y.; Jing, K.; Jiang, Y.-X.; Bo, Z.-Y.; Lan, Y.; Li J.; Yu, D.-G. J. Am. Chem. Soc. 2019, 141, 18825.
[60] Qiu, J.; Gao, S.; Li, C.; Zhang, L.; Wang, Z.; Wang, X.; Ding, K.-L. Chem.-Eur. J. 2019, 25, 13874.
[61] Feroci, M.; Orsini, M.; Palombi, L.; Sotgiu, G.; Colapietro, M.; Inesi, A. J. Org. Chem. 2004, 69, 487.
[62] Orsini, M.; Feroci, M.; Sotgiuand. G.; Inesi, A. Org. Biomol. Chem. 2005, 3, 1202.
[63] Zhang, K.; Wang, H.; Zhao, S.-F.; Niu D.-F.; Lu, J.-X. J. Electroanal. Chem. 2009, 630, 35.
[64] Chen, B.-L.; Tu, Z.-Y.; Zhu, H.-W.; Sun, W.-W.; Wang, H.; Lu, J.-X. Electrochim. Acta 2014, 116, 475.
[65] He, Q.; O'Brien, J.-W.; Kitselman, K.-A.; Tompkins, L.-E.; Curtis G.-C.-T.; Kerton, F.-M. Catal. Sci. Technol. 2014, 4, 1513.
[66] Sakakura, T.; Kohnoa, K. Chem. Commun. 2009, 45, 1312.
[67] Chen, B.-L.; Zhu, H.-W.; Xiao, Y.; Sun, Q.-L.; Wang, H.; Lu, J.-X. Electrochem. Commun. 2014, 42, 55.
[68] Yang, H.-P.; Yue, Y.-N.; Sun, Q.-L.; Feng, Q.; Wang, H.; Lu, J.-X. Chem. Commun. 2015, 51, 12216.
[69] Jiao, K.-J.; Li, Z.-M.; Xu, X.-T.; Zhang, L.-P.; Li, Y.; Zhang, K.; Mei, T.-S. Org. Chem. Front. 2018, 5, 2244.
[70] Song, Q.-W.; Liu, P.; Han, L.-H.; Zhang K.; He, L.-N. Chin. J. Chem. 2018, 36, 147.
[71] Niu, D.-F.; Xiao, L.-P.; Zhang, A.-J.; Zhang, G.-R.; Tan, Q.-Y.; Lu, J.-X. Tetrahedron 2008, 64, 10517.
[72] Isse, A.; Gennaro, A.; Vianello, E. J. Chem. Soc., Dalton Trans. 1996, 1613.
[73] Takeichi, T.; Ozaki, Y.; Takayama, Y. Chem. Lett. 1987, 1137.
[74] Yoshida, M.; Fujita, M.; Ishii, T.; Ihara, M. J. Am. Chem. Soc. 2003, 125, 4874.
[75] Yoshida, S.; Fukui, K.; Kikuchi, S.; Yamada, T. J. Am. Chem. Soc. 2010, 132, 4072.
[76] Yamada, W.; Sugawara, Y.; Cheng, H.-M. Ikeno, T.; Yamada, T. Eur. J. Org. Chem. 2007, 2007, 2604.
[77] Vara, B.-A.; Struble, T.-J.; Wang, W.; Dobish, M.-C.; Johnston, J.-N. J. Am. Chem. Soc. 2015, 137, 7302.
[78] Yousefi, R.; Struble, T.-J.; Payne, J.-L.; Vishe, M.; Schley, N.-D.; Johnston, J.-N. J. Am. Chem. Soc. 2019, 141, 618.
[79] Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588.
[80] Gao, X.-T.; Xie, S.-L.; Zhou, F.; Wu, H.-H.; Zhou, J. Chem. Commun. 2019, 55, 14303.
[81] Xie, S.; Gao, X.; Zhou, F.; Wu, H.; Zhou, J. Chin. Chem. Lett. 2020, 31, 324.
[82] Hartwig, J.-F.; Pouy, M.-J. Top. Organomet. Chem. 2011, 34, 169.
[83] Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2012, 38, 155.
[84] Qu, J.; Helmchen, G. Acc. Chem. Res. 2017, 50, 2539.
[85] Zhang, X.; Liu, W.-B.; Cheng, Q.; You, S.-L. Organometallics 2016, 35, 2467.
[86] Zhuo, C.-X.; Zhang X.; You, S.-L. ACS Catal. 2016, 6, 5307.
[87] Ye, K.-Y.; He, H.; Liu, W.-B.; Dai, L.-X.; Helmchen, G.; You, S.-L. J. Am. Chem. Soc. 2011, 133, 19006.
[88] Roggen, M.; Carreira, E.-M. J. Am. Chem. Soc. 2010, 132, 11917.
[89] Xia, J.-B.; Liu, W.-B.; Wang, T.-M.; You, S.-L. Chem.-Eur. J. 2010, 16, 6442.
[90] Yamashita, Y.; Gopalarathnam, A; Hartwig, J.-F. J. Am. Chem. Soc. 2007, 129, 7508.
[91] Nemoto, T.; Sakamoto, T.; Matsumoto T.; Hamada, Y. Tetrahedron Lett. 2006, 47, 8737.
[92] Welter, C.; Moreno, R.-M.; Streiff, S.; Helmchen, G. Org. Biomol. Chem. 2005, 3, 3266.
[93] Zheng, S.-C.; Zhang, M.; Zhao, X.-M. Chem.-Eur. J. 2014, 20, 7216.
[94] Zhang, M.; Zhao X.; Zheng, S. Chem. Commun. 2014, 50, 4455.
[95] Liu, W.-B.; He, H.; Dai, L.-X.; You, S.-L. Synthesis 2009, 2076.

不对称催化实现的二氧化碳固定直接合成光学活性小分子的最新进展

Recent Advances of CO₂ Fixation via Asymmetric Catalysis for the Direct Synthesis of Optically Active Small Molecules

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	杨爽, 房新强. 氮杂环卡宾催化实现的动力学拆分近期研究进展[J]. 有机化学, 2024, 44(2): 448-480.
[2]	陈宛婷, 钟雄威, 邢佳乐, 吴昌书, 高杨. C—N轴手性化合物的不对称催化合成研究进展[J]. 有机化学, 2024, 44(2): 349-377.
[3]	姜权彬. 经由氮杂邻联烯醌中间体合成轴手性化合物的研究进展[J]. 有机化学, 2024, 44(1): 159-172.
[4]	张俊杰, 徐学涛. (S)-(–)-Xylopinine和(S)-(+)-Laudanosine的不对称合成[J]. 有机化学, 2023, 43(9): 3297-3303.
[5]	程春霞, 吴露平, 沙风, 伍新燕. 手性叔膦-酰胺不对称催化香豆素与Morita-Baylis-Hillman碳酸酯之间的插烯烯丙基烷基化反应[J]. 有机化学, 2023, 43(9): 3188-3195.
[6]	张素珍, 张文文, 杨慧, 顾庆, 游书力. 铑催化2-烯基苯酚与炔烃的对映体选择性螺环化反应[J]. 有机化学, 2023, 43(8): 2926-2933.
[7]	廖旭, 王泽宇, 唐武飞, 林金清. 多孔有机聚合物用于化学固定二氧化碳的研究进展[J]. 有机化学, 2023, 43(8): 2699-2710.
[8]	刘露, 张曙光, 胡仁威, 赵晓晓, 崔京南, 贡卫涛. 基于多羟基柱[5]芳烃的酚醛多孔聚合物合成及CO₂催化转化[J]. 有机化学, 2023, 43(8): 2808-2814.
[9]	陈玉琢, 孙红梅, 王亮, 胡方芝, 李帅帅. 基于α-氢迁移策略构建杂环骨架的研究进展[J]. 有机化学, 2023, 43(7): 2323-2337.
[10]	罗诚, 尹艳丽, 江智勇. P-手性膦氧化物的不对称合成研究进展[J]. 有机化学, 2023, 43(6): 1963-1976.
[11]	孙李星, 孙婷婷, 王海清, 吴淑芳, 王小烨, 刘天雅, 张宇辰. Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应[J]. 有机化学, 2023, 43(6): 2178-2188.
[12]	宋姿洁, 刘俊, 白赢, 厉嘉云, 彭家建. 利用硅氢加成反应催化转化二氧化碳研究进展[J]. 有机化学, 2023, 43(6): 2068-2080.
[13]	任志军, 罗维纬, 周俊. 银介导的N-芳基丙烯酰胺串联环化反应研究进展[J]. 有机化学, 2023, 43(6): 2026-2039.
[14]	李靖鹏, 黄顺桃, 杨棋, 李伟强, 刘腾, 黄超. 利用连续流动技术合成(Z)-N-乙烯基取代N,O-缩醛[J]. 有机化学, 2023, 43(4): 1550-1558.
[15]	南江, 黄冠杰, 胡岩, 王波. 钌催化喹唑啉酮与碳酸亚乙烯酯的C—H [4＋2]环化反应[J]. 有机化学, 2023, 43(4): 1537-1549.

不对称催化实现的二氧化碳固定直接合成光学活性小分子的最新进展

Recent Advances of CO2 Fixation via Asymmetric Catalysis for the Direct Synthesis of Optically Active Small Molecules

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

Recent Advances of CO₂ Fixation via Asymmetric Catalysis for the Direct Synthesis of Optically Active Small Molecules