氮杂环化合物的多相催化加氢反应及其可逆脱氢反应的最新进展

doi:10.1016/S1872-2067(19)63336-X

摘要/Abstract

摘要：

功能化1，2，3，4-四氢喹啉类化合物在医药、生物碱、农药和许多精细化学品的生产中作为具有生物活性的构筑单元和关键中间体，其合成越来越受到人们的关注.通过喹啉化合物的选择性加氢得到py-THQs具有高的原子效率，是一种直接和有效的方法.喹啉化合物的选择性加氢常面临以下问题和挑战：（1）喹啉类化合物的加氢反应具有较高的反应能垒，使得反应需要在苛刻的反应条件下进行；（2）加氢反应过程通常涉及多个中间体，可能会产生副产物；（3）取代喹啉类化合物如乙烯基、酮基、腈基、醛基、氨基、卤素等易还原取代基也可能发生氢化反应，导致选择性下降；（4）由于N-杂环中金属与N原子的强配位效应，催化活性位点易中毒，导致催化剂的可重用性较差.新型、高性能非均相催化剂的开发得到了不断关注，近期取得了一系列进展.
氮杂环化合物的催化脱氢也是有机合成的关键步骤，所得到的不饱和氮杂环化合物是各种生物活性化合物和药物的重要合成中间体.同时，从氢气存储的角度出发，有机分子的可逆加氢/脱氢被认为是液体有机储氢系统中一个很有前途的策略.氮杂环化合物的脱氢（释放氢气）和加氢（储存氢气）相结合，构建了一个有效的液态有机氢存储体系.研制一种能够实现氮杂环化合物可逆脱氢/加氢的催化剂越来越受到人们的关注.
近几十年来，功能化喹啉化合物选择性加氢高效多相催化剂的可控合成取得了重大突破，使人们能够从整体上关联结构-性能关系.本文综述了近年来该领域在催化剂合成策略、微观结构和化学特性、催化性能评价及其内在关系等方面取得的重要进展.本文首先介绍了单贵金属催化剂（Pd，Pt，Ru，Rh，Ir，Au）和双/多金属催化剂（RuCu，AuPd，PdNi）的研究现状，然后对储量丰富的廉价金属催化剂（Co，Fe，Ni，Cu）进行了综述.综合文献结论，反应介质、载体的性质、金属-载体相互作用、活性金属的电子结构、双金属或多金属协同效应、微观结构（核壳、包覆、蛋黄结构）以及纳米粒子的粒径大小对催化剂的最终催化行为起着重要作用.最后，引入氮杂环化合物的脱氢反应，形成一个可逆的加氢/脱氢体系用于液相有机氢储存系统，并对其反应机理及今后的研究方向进行了探讨.本综述将加深我们对氮杂环化合物催化转化的认识，为研究人员合理设计催化剂提供指导.

关键词: 氮杂环化合物, 选择性加氢, 脱氢反应, 多相催化剂, 构-效关系

Abstract:

The selective hydrogenation of quinolines to 1,2,3,4-tetrahydroquinolines (py-THQ) and its derivatives has attracted a considerable amount of attention as they show great versatility in many pharmaceuticals, agrochemicals, and fine chemicals. Over the past few decades, great breakthroughs have been achieved in the controlled synthesis of efficient heterogeneous catalysts used for the selective hydrogenation of functionalized quinoline compounds, which allow one to correlate the structure-property relationships. In this review, we will summarize the recent significant progress achieved in this field covering the synthetic strategies, microstructural and chemical features, catalytic performance, and internal relationships. State-of-the-art noble metal-based single (Pd, Pt, Ru, Rh, Ir and Au) and bi/multi-metallic catalysts (RuCu, AuPd, and PdNi) are first introduced, followed by a summary of earth-abundant metal-based catalysts (Co, Fe, Ni, and Cu). Finally, the dehydrogenation of N-heterocycles is introduced to form a reversible hydrogenation/dehydrogenation system for H₂ storage, which can be employed in a liquid organic hydrogen system. Furthermore, the reaction mechanism and future research direction in these areas are also discussed. This review will deepen our understanding of the catalytic transformation of N-heterocycles and provide guidance for researchers on the rational design of catalysts.

Key words: N-heterocycles, Selective hydrogenation, Dehydrogenation, Heterogeneous catalysts, Structure-activity relationship

魏中哲, 邵方君, 王建国. 氮杂环化合物的多相催化加氢反应及其可逆脱氢反应的最新进展[J]. 催化学报, 2019, 40(7): 980-1002.

Zhongzhe Wei, Fangjun Shao, Jianguo Wang. Recent advances in heterogeneous catalytic hydrogenation and dehydrogenation of N-heterocycles[J]. Chinese Journal of Catalysis, 2019, 40(7): 980-1002.

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参考文献

[1] V. Sridharan, P. A. Suryavanshi, J. C. Menéndez, Chem. Rev., 2011, 111, 7157-7259.
[2] L. Tao, Q. Zhang, S. S. Li, X. Liu, Y. M. Liu, Y. Cao, Adv. Synth. Catal., 2015, 357, 753-760.
[3] B. Vilhanová, J. A. van Bokhoven, M. Ranocchiari, Adv. Synth. Catal., 2016, 359, 677-686.
[4] R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider, Y. Fort, Org. Lett., 2003, 5, 2311-2314.
[5] T. Kubo, C. Katoh, K. Yamada, K. Okano, H. Tokuyama, T. Fukuyama, Tetrahedron, 2008, 64, 11230-11236.
[6] K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, H. Yamamoto, J. Am. Chem. Soc., 1983, 105, 2831-2843.
[7] R. H. Fish, A. D. Thormodsen, G. A. Cremer, J. Am. Chem. Soc., 1982, 104, 5234-5237.
[8] T. Wang, L. G. Zhuo, Z. Li, F. Chen, Z. Ding, Y. He, Q. H. Fan, J. Xiang, Z. X. Yu, A. S. C. Chan, J. Am. Chem. Soc., 2011, 133, 9878-9891.
[9] R. Kuwano, R. Ikeda, K. Hirasada, Chem. Commun., 2015, 51, 7558-7561.
[10] G. E. Dobereiner, A. Nova, N. D. Schley, N. Hazari, S. J. Miller, O. Eisenstein, R. H. Crabtree, J. Am. Chem. Soc., 2011, 133, 7547-7562.
[11] C. Xu, L. Zhang, C. Dong, J. Xu, Y. Pan, Y. Li, H. Zhang, H. Li, Z. Yu, L. Xu, Adv. Synth. Catal., 2016, 358, 567-572.
[12] S. Fleischer, S. Zhou, S. Werkmeister, K. Junge, M. Beller, Chem. Eur. J., 2013, 19, 4997-5003.
[13] L. Zhang, R. Qiu, X. Xue, Y. Pan, C. Xu, H. Li, L. Xu, Adv. Synth. Catal., 2015, 357, 3529-3537.
[14] X. F. Tu, L. Z. Gong, Angew. Chem. Int. Ed., 2012, 51, 11346-11349.
[15] R. Xu, S. Chakraborty, H. Yuan, W. D. Jones, ACS Catal., 2015, 5, 6350-6354.
[16] D. S. Wang, Q. A. Chen, S. M. Lu, Y. G. Zhou, Chem. Rev., 2012, 112, 2557-2590.
[17] Y. T. Gong, M. M. Li, H. R. Li, Y. Wang, Green Chem., 2015, 17, 715-736.
[18] J. J. Bravo-Suárez, R. V. Chaudhari, B. Subramaniam, ACS Symposium Series, 2013, 1132, 3-68.
[19] M. Campanati, A. Vaccari, O. Piccolo, J. Mol. Catal. A, 2002, 179, 287-292.
[20] R. Rahi, M. Fang, A. Ahmed, R. A. Sanchez-Delgado, Dalton Trans., 2012, 41, 14490-14497.
[21] Y. Gong, P. Zhang, X. Xu, Y. Li, H. Li, Y. Wang, J. Catal., 2013, 297, 272-280.
[22] M. Guo, C. Li, Q. Yang, Catal. Sci. Technol., 2017, 7, 2221-2227.
[23] M. M. Dell'Anna, V. F. Capodiferro, M. Mali, D. Manno, P. Cotugno, A. Monopoli, P. Mastrorilli, Appl. Catal., A, 2014, 481, 89-95.
[24] Y. Zhang, J. Zhu, Y. T. Xia, X. T. Sun, L. Wu, Adv. Synth. Catal., 2016, 358, 3039-3045.
[25] N. Hashimoto, Y. Takahashi, T. Hara, S. Shimazu, T. Mitsudome, T. Mizugaki, K. Jitsukawa, K. Kaneda, Chem. Lett., 2010, 39, 832-834.
[26] L. Bai, X. Wang, Q. Chen, Y. Ye, H. Zheng, J. Guo, Y. Yin, C. Gao, Angew. Chem. Int. Ed., 2016, 55, 15656-15661.
[27] S. Li, Y. Yang, Y. Wang, H. Liu, J. Tai, J. Zhang, B. Han, Catal. Sci. Technol., 2018, 8, 4314-4317.
[28] C. Bianchini, V. Dal Santo, A. Meli, S. Moneti, M. Moreno, W. Oberhauser, R. Psaro, L. Sordelli, F. Vizza, J. Catal., 2003, 213, 47-62.
[29] M. Fang, R.A. Sanchez-Delgado, J. Catal., 2014, 311, 357-368.
[30] M. Fang, N. Machalaba, R. A. Sanchez-Delgado, Dalton Trans., 2011, 40, 10621-10632.
[31] H. Konnerth, M. H. G. Prechtl, Green Chem., 2017, 19, 2762-2767.
[32] X. Yu, R. Nie, H. Zhang, X. Lu, D. Zhou, Q. Xia, Microporous Mesoporous Mater., 2018, 256, 10-17.
[33] P. Barbaro, L. Gonsalvi, A. Guerriero, F. Liguori, Green Chem., 2012, 14, 3211-3219.
[34] M. Nasiruzzaman Shaikh, M. A. Aziz, A. N. Kalanthoden, A. Helal, A. S. Hakeem, M. Bououdina, Catal. Sci. Technol., 2018, 8, 4709-4717.
[35] J. F. Zhang, R. Zhong, Q. Zhou, X. Hong, S. Huang, H. Z. Cui, X. F. Hou, ChemCatChem, 2017, 9, 2496-2505.
[36] A. Karakulina, A. Gopakumar, Z. F. Fei, P. J. Dyson, Catal. Sci. Technol., 2018, 8, 5091-5097.
[37] F. Zhang, C. Ma, S. Chen, J. Zhang, Z. Li, X. M. Zhang, Mol. Catal., 2018, 452, 145-153.
[38] S. Zhang, Z. Xia, T. Ni, Z. Zhang, Y. Ma, Y. Qu, J. Catal., 2018, 359, 101-111.
[39] L. Zhang, X. Y. Wang, Y. Xue, X. J. Zeng, H. Chen, R. X. Li, S. L. Wang, Catal. Sci. Technol., 2014, 4, 1939-1948.
[40] T. N. Ye, J. Li, M. Kitano, H. Hosono, Green Chem., 2017, 19, 749-756.
[41] Y. G. Ji, K. Wei, T. Liu, L. Wu, W. H. Zhang, Adv. Synth. Catal., 2017, 359, 933-940.
[42] A. Karakulina, A. Gopakumar, ?. Akçok, B. L. Roulier, T. LaGrange, S. A. Katsyuba, S. Das, P. J. Dyson, Angew. Chem. Int. Ed., 2016, 55, 292-296.
[43] D. Ren, L. He, L. Yu, R. S. Ding, Y. M. Liu, Y. Cao, H. Y. He, K. N. Fan, J. Am. Chem. Soc., 2012, 134, 17592-17598.
[44] Y. Mikami, K. Ebata, T. Mitsudome, T. Mizugaki, K. Jitsukawa, K. Kaneda, Heterocycles, 2011, 82, 1371-+.
[45] F. Chen, A. E. Surkus, L. He, M. M. Pohl, J. Radnik, C. Topf, K. Junge, M. Beller, J. Am. Chem. Soc., 2015, 137, 11718-11724.
[46] C. Deraedt, R. Ye, W. T. Ralston, F. D. Toste, G. A. Somorjai, J. Am. Chem. Soc., 2017, 139, 18084-18092.
[47] D. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. Int. Ed., 2005, 44, 7852-7872.
[48] P. Gélin, M. Primet, Appl. Catal. B, 2002, 39, 1-37.
[49] S. Enthaler, K. Junge, M. Beller, Angew. Chem. Int. Ed., 2008, 47, 3317-3321.
[50] K. S. Egorova, V. P. Ananikov, Angew. Chem. Int. Ed., 2016, 55, 12150-12162.
[51] S. Zhang, Z. M. Xia, T. Ni, H. Zhang, C. Wu, Y. Q. Qu, J. Mater. Chem. A, 2017, 5, 3260-3266.
[52] T. Mitsui, M. K. Rose, E. Fomin, D. F. Ogletree, M. Salmeron, Nature, 2003, 422, 705-707.
[53] Z. Hou, N. Theyssen, W. Leitner, Green Chem., 2007, 9, 127-132.
[54] X. Xu, Y. Li, Y. Gong, P. Zhang, H. Li, Y. Wang, J. Am. Chem. Soc., 2012, 134, 16987-16990.
[55] P. Zhang, Y. Gong, H. Li, Z. Chen, Y. Wang, Nat. Commun., 2013, 4, 1593.
[56] Y. Zhang, M. Mao, Y. G. Ji, J. Zhu, L. Wu, Tetrahedron Lett., 2016, 57, 329-332.
[57] K. Okamoto, R. Akiyama, H. Yoshida, T. Yoshida, S. Kobayashi, J. Am. Chem. Soc., 2005, 127, 2125-2135.
[58] H. Mao, C. Chen, X. P. Liao, B. Shi, J. Mol. Catal. A, 2011, 341, 51-56.
[59] H. Mao, J. Ma, Y. Liao, S. Zhao, X. Liao, Catal. Sci. Technol., 2013, 3, 1612-1617.
[60] D. S. Deng, G. Q. Han, X. Zhu, X. Xu, Y. T. Gong, Y. Wang, Chin. Chem. Lett., 2015, 26, 277-281.
[61] Y. S. Ren, Y. X. Wang, X. Li, Z. H. Zhang, Q. Chi, New J. Chem., 2018, 42, 16694-16702.
[62] P. Strasser, M. Gliech, S. Kuehl, T. Moeller, Chem. Soc. Rev., 2018, 47, 715-735.
[63] J. Lyu, J. Wang, C. Lu, L. Ma, Q. Zhang, X. He, X. Li, J. Phys. Chem. C, 2014, 118, 2594-2601.
[64] H. Liu, M. Liang, C. Xiao, N. Zheng, X. Feng, Y. Liu, J. Xie, Y. Wang, J. Mol. Catal. A, 2009, 308, 79-86.
[65] Y. Wang, X. Wang, M. Antonietti, Angew. Chem. Int. Ed., 2011, 51, 68-89.
[66] Y. Gong, M. Li, H. Li, Y. Wang, Green Chem., 2015, 17, 715-736.
[67] Y. Wang, J. Yao, H. Li, D. Su, M. Antonietti, J. Am. Chem. Soc., 2011, 133, 2362-2365.
[68] Z. Wei, Y. Gong, T. Xiong, P. Zhang, H. Li, Y. Wang, Catal. Sci. Technol., 2015, 5, 397-404.
[69] C. Michel, J. Zaffran, A. M. Ruppert, J. Matras-Michalska, M. J?drzejczyk, J. Grams, P. Sautet, Chem. Commun., 2014, 50, 12450-12453.
[70] M. Li, F. Xu, H. Li, Y. Wang, Catal. Sci. Technol., 2016, 6, 3670-3693.
[71] Z. Wei, J. Wang, S. Mao, D. Su, H. Jin, Y. Wang, F. Xu, H. Li, Y. Wang, ACS Catal., 2015, 5, 4783-4789.
[72] Z. Wei, Y. Chen, J. Wang, D. Su, M. Tang, S. Mao, Y. Wang, ACS Catal., 2016, 6, 5816-5822.
[73] J. Wang, F. Xu, H. Jin, Y. Chen, Y. Wang, Adv. Mater., 2017, 29, 1605838.
[74] X. H. Li, M. Antonietti, Chem. Soc. Rev., 2013, 42, 6593-6604.
[75] J. S. Lee, X. Wang, H. Luo, G. A. Baker, S. Dai, J. Am. Chem. Soc., 2009, 131, 4596-4597.
[76] J. Deng, T. Xiong, F. Xu, M. Li, C. Han, Y. Gong, H. Wang, Y. Wang, Green Chem., 2015, 17, 4053-4060.
[77] M. H. Sun, S. Z. Huang, L. H. Chen, Y. Li, X. Y. Yang, Z. Y. Yuan, B. L. Su, Chem. Soc. Rev., 2016, 45, 3479-3563.
[78] Z. Z. Wei, X. F. Li, J. Deng, J. Wang, H. R. Li, Y. Wang, Mol. Catal., 2018, 448, 100-107.
[79] X. L. Yu, R. F. Nie, H. F. Zhang, X. H. Lu, D. Zhou, Q. H. Xia, Microporous Mesoporous Mater., 2018, 256, 10-17.
[80] K. M. Kosuda, A. Wittstock, C. M. Friend, M. Bäumer, Angew. Chem. Int. Ed., 2012, 51, 1698-1701.
[81] Y. Lu, X. Feng, B. S. Takale, Y. Yamamoto, W. Zhang, M. Bao, ACS Catal., 2017, 7, 8296-8303.
[82] M. Zhao, Y. Ji, M. Y. Wang, N. Zhong, Z. N. Kang, N. Asao, W. J. Jiang, Q. Chen, ACS Appl. Mater. Interfaces, 2017, 9, 34804-34811.
[83] Y. Lu, Y. Yamamoto, A. I. Almansour, N. Arumugam, R. S. Kumar, M. Bao, Chin. J. Catal., 2018, 39, 1746-1752.
[84] J. Y. Chen, B. Lim, E. P. Lee, Y. N. Xia, Nano Today, 2009, 4, 81-95.
[85] W. T. Yu, M. D. Porosoff, J. G. G. Chen, Chem. Rev., 2012, 112, 5780-5817.
[86] X. Xue, M. Zeng, Y. Wang, Appl. Catal. A, 2018, 560, 37-41.
[87] C. T. Campbell, Nat. Chem., 2012, 4, 597-598.
[88] J. Pritchard, G. A. Filonenko, R. van Putten, E. J. M. Hensen, E. A. Pidko, Chem. Soc. Rev., 2015, 44, 3808-3833.
[89] A. Dhakshinamoorthy, H. Garcia, Chem. Soc. Rev., 2012, 41, 5262-5284.
[90] J. Wang, Z. Wei, S. Mao, H. Li, Y. Wang, Energy Environ. Sci, 2018, 11, 800-806.
[91] J. Yang, B. X. Chen, X. K. Liu, W. Liu, Z. J. Li, J. C. Dong, W. X. Chen, W. S. Yan, T. Yao, X. Z. Duan, Y. Wu, Y. D. Li, Angew. Chem., Int. Ed., 2018, 57, 9495-9500.
[92] R. A. Sánchez-Delgado, N. Machalaba, N. Ng-a-qui, Catal. Commun., 2007, 8, 2115-2118.
[93] Y. L. Cao, B. W. Zhao, X. B. Bao, Y. Wang, ACS Catal., 2018, 8, 7077-7085.
[94] L. Zhou, X. Qi, X. Jiang, Y. Zhou, H. Fu, H. Chen, J. Colloid Interface Sci., 2013, 392, 201-205.
[95] H. Y. Jiang, X. X. Zheng, Catal. Sci. Technol., 2015, 5, 3728-3734.
[96] X. Wang, W. Chen, L. Zhang, T. Yao, W. Liu, Y. Lin, H. Ju, J. Dong, L. Zheng, W. Yan, X. Zheng, Z. Li, X. Wang, J. Yang, D. He, Y. Wang, Z. Deng, Y. Wu, Y. Li, J. Am. Chem. Soc., 2017, 139, 9419-9422.
[97] B. T. Qiao, A. Q. Wang, X. F. Yang, L. F. Allard, Z. Jiang, Y. T. Cui, J. Y. Liu, J. Li, T. Zhang, Nat. Chem., 2011, 3, 634-641.
[98] X. F. Yang, A. Q. Wang, B. T. Qiao, J. Li, J. Y. Liu, T. Zhang, Acc. Chem. Res., 2013, 46, 1740-1748.
[99] J. Jones, H. F. Xiong, A. T. Delariva, E. J. Peterson, H. Pham, S. R. Challa, G. S. Qi, S. Oh, M. H. Wiebenga, X. I. P. Hernandez, Y. Wang, A. K. Datye, Science, 2016, 353, 150-154.
[100] M. Campanati, M. Casagrande, I. Fagiolino, M. Lenarda, L. Storaro, M. Battagliarin, A. Vaccari, J. Mol. Catal. A, 2002, 184, 267-272.
[101] G. Y. Fan, J. Wu, Catal. Commun., 2013, 31, 81-85.
[102] H. U. Blaser, H. P. Jalett, W. Lottenbach, M. Studer, J. Am. Chem. Soc., 2000, 122, 12675-12682.
[103] Y. P. Sun, H. Y. Fu, D. L. Zhang, R. X. Li, H. Chen, X. J. Li, Catal. Commun., 2010, 12, 188-192.
[104] B. Sun, F. A. Khan, A. Vallat, G. Süss-Fink, Appl. Catal. A, 2013, 467, 310-314.
[105] D. Zhu, H. Jiang, L. Zhang, X. Zheng, H. Fu, M. Yuan, H. Chen, R. Li, ChemCatChem, 2014, 6, 2954-2960.
[106] A. Sánchez, M. Fang, A. Ahmed, R. A. Sánchez-Delgado, Appl. Catal. A, 2014, 477, 117-124.
[107] H. Y. Jiang, X. X. Zheng, Appl. Catal. A, 2015, 499, 118-123.
[108] M. Niu, Y. Wang, P. Chen, D. Du, J. Jiang, Z. Jin, Catal. Sci. Technol., 2015, 5, 4746-4749.
[109] A. Stephen, K. Hashmi, G. J. Hutchings, Angew. Chem., Int. Ed., 2006, 45, 7896-7936.
[110] A. Corma, H. Garcia, Chem. Soc. Rev., 2008, 37, 2096-2126.
[111] R. Ciriminna, E. Falletta, C. Della Pina, J. H. Teles, M. Pagliaro, Angew. Chem. Int. Ed., 2016, 55, 14210-14217.
[112] R. Ghosh Chaudhuri, S. Paria, Chem. Rev., 2012, 112, 2373-2433.
[113] J. Li, G. Wang, J. Wang, S. Miao, M. Wei, F. Yang, L. Yu, X. Bao, Nano Res., 2014, 7, 1519-1527.
[114] C. J. Pollock, S. DeBeer, Acc. Chem. Res., 2015, 48, 2967-2975.
[115] N. A. Beckers, S. Huynh, X. Zhang, E. J. Luber, J. M. Buriak, ACS Catal., 2012, 2, 1524-1534.
[116] Y. Chen, Z. Yu, Z. Chen, R. Shen, Y. Wang, X. Cao, Q. Peng, Y. Li, Nano Res., 2016, 9, 2632-2640.
[117] M. Yan, T. A. Jin, Q. Chen, H. E. Ho, T. Fujita, L. Y. Chen, M. Bao, M. W. Chen, N. Asao, Y. Yamamoto, Org. Lett., 2013, 15, 1484-1487.
[118] K. S. Egorova, V. P. Ananikov, Angew. Chem. Int. Ed., 2016, 55, 12150-12162.
[119] D. Wang, D. Astruc, Chem. Soc. Rev., 2017, 46, 816-854.
[120] M. R. Friedfeld, M. Shevlin, J. M. Hoyt, S. W. Krska, M. T. Tudge, P. J. Chirik, Science, 2013, 342, 1076-1080.
[121] R. M. Bullock, Science, 2013, 342, 1054-1055.
[122] Z. Wei, Y. Li, J. Wang, H. Li, Y. Wang, Chin. Chem. Lett., 2018, 29, 815-818.
[123] Z. Wei, S. Mao, F. Sun, J. Wang, B. Mei, Y. Chen, H. Li, Y. Wang, Green Chem., 2018, 20, 671-679.
[124] W. M. Czaplik, J. M. Neudorfl, A. J. von Wangelin, Green Chem., 2007, 9, 1163-1165.
[125] C. Liu, Z. Rong, Z. Sun, Y. Wang, W. Du, Y. Wang, L. Lu, RSC Adv., 2013, 3, 23984-23988.
[126] P. Büschelberger, E. Reyes-Rodriguez, C. Schöttle, J. Treptow, C. Feldmann, A. Jacobi von Wangelin, R. Wolf, Catal. Sci. Technol., 2018, 8, 2648-2653.
[127] I. Sorribes, L. C. Liu, A. Domenech-Carbo, A. Corma, ACS Catal., 2018, 8, 4545-4557.
[128] F. Chen, W. Li, B. Sahoo, C. Kreyenschulte, G. Agostini, H. Lund, K. Junge, M. Beller, Angew. Chem., Int. Ed., 2018, 57, 14488-14492.
[129] J. R. Cabrero-Antonino, R. Adam, K. Junge, R. Jackstell, M. Beller, Catal. Sci. Technol., 2017, 7, 1981-1985.
[130] F. Chen, B. Sahoo, C. Kreyenschulte, H. Lund, M. Zeng, L. He, K. Junge, M. Beller, Chem. Sci., 2017, 8, 6239-6246.
[131] G. Q. Li, H. H. Yang, H. F. Zhang, Z. Y. Qi, M. D. Chen, W. Hu, L. H. Tian, R. F. Nie, W. Y. Huang, ACS Catal., 2018, 8, 8396-8405.
[132] B. Sahoo, C. Kreyenschulte, G. Agostini, H. Lund, S. Bachmann, M. Scalone, K. Junge, M. Beller, Chem. Sci., 2018, 9, 8134-8141.
[133] R. V. Jagadeesh, A. E. Surkus, H. Junge, M. M. Pohl, J. Radnik, J. Rabeah, H. Huan, V. Schuenemann, A. Brueckner, M. Beller, Science, 2013, 342, 1073-1076.
[134] X. J. Cui, Y. H. Li, S. Bachmann, M. Scalone, A. E. Surkus, K. Junge, C. Topf, M. Beller, J. Am. Chem. Soc., 2015, 137, 10652-10658.
[135] F. A. Westerhaus, R. V. Jagadeesh, G. Wienhofer, M. M. Pohl, J. Radnik, A. E. Surkus, J. Rabeah, K. Junge, H. Junge, M. Nielsen, A. Bruckner, M. Beller, Nat. Chem., 2013, 5, 537-543.
[136] G. Shi, J. Shen, J. Mater. Chem., 2009, 19, 2295-2297.
[137] J. S. M. Samec, J. E. Backvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev., 2006, 35, 237-248.
[138] L. Aschwanden, T. Mallat, F. Krumeich, A. Baiker, J. Mol. Catal. A, 2009, 309, 57-62.
[139] D. V. Jawale, E. Gravel, N. Shah, V. Dauvois, H. Y. Li, I. N. N. Namboothiri, E. Doris, Chem. Eur. J., 2015, 21, 7039-7042.
[140] D. Ge, L. Hu, J. Wang, X. Li, F. Qi, J. Lu, X. Cao, H. Gu, ChemCatChem, 2013, 5, 2183-2186.
[141] S. K. Moromi, S. M. A. H. Siddiki, K. Kon, T. Toyao, K. I. Shimizu, Catal. Today, 2017, 281, 507-511.
[142] M. Amende, C. Gleichweit, K. Werner, S. Schernich, W. Zhao, M. P. A. Lorenz, O. Höfert, C. Papp, M. Koch, P. Wasserscheid, M. Laurin, H. P. Steinrück, J. Libuda, ACS Catal., 2014, 4, 657-665.
[143] J. W. Zhang, D. D. Li, G. P. Lu, T. Deng, C. Cai, ChemCatChem, 2018, 10, 4980-4986.
[144] T. Hara, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Tetrahedron Lett., 2003, 44, 6207-6210.
[145] D. Damodara, R. Arundhathi, P. R. Likhar, Adv. Synth. Catal., 2014, 356, 189-198.
[146] J. Li, G. Liu, X. Long, G. Gao, J. Wu, F. Li, J. Catal., 2017, 355, 53-62.
[147] Y. H. Han, Z. Y. Wang, R. R. Xu, W. Zhang, W. X. Chen, L. R. Zheng, J. Zhang, J. Luo, K. L. Wu, Y. Q. Zhu, C. Chen, Q. Peng, Q. Liu, P. Hu, D. S. Wang, Y. D. Li, Angew. Chem., Int. Ed., 2018, 57, 11262-11266.
[148] A. V. Iosub, S. S. Stahl, Org. Lett., 2015, 17, 4404-4407.
[149] K. Mullick, S. Biswas, A. M. Angeles-Boza, S. L. Suib, Chem. Commun., 2017, 53, 2256-2259.
[150] W. Y. Zhou, Q. Y. Tao, F. A. Sun, X. B. Cao, J. F. Qian, J. Xu, M. Y. He, Q. Chen, J. L. Xiao, J. Catal., 2018, 361, 1-11.
[151] J. Y. Zhang, S. Y. Chen, F. F. Chen, W. S. Xu, G. J. Deng, H. Gong, Adv. Synth. Catal., 2017, 359, 2358-2363.
[152] Y. J. Zhang, S. F. Pang, Z. H. Wei, H. J. Jiao, X. C. Dai, H. L. Wang, F. Shi, Nat. Commun., 2018, 9, 1465.
[153] F. Su, S. C. Mathew, L. Möhlmann, M. Antonietti, X. Wang, S. Blechert, Angew. Chem. Int. Ed., 2010, 50, 657-660.
[154] J. L. Li, G. L. Liu, X. D. Long, G. Gao, J. Wu, F. W. Li, J. Catal., 2017, 355, 53-62.
[155] P. Ryabchuk, G. Agostini, M. M. Pohl, H. Lund, A. Agapova, H. Junge, K. Junge, M. Beller, Sci. Adv., 2018, 4, eaat0761/1-eaat0761/10.