Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode

doi:10.1016/S1872-2067(21)63834-2

Chinese Journal of Catalysis ›› 2021, Vol. 42 ›› Issue (11): 1983-1991.DOI: 10.1016/S1872-2067(21)63834-2

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Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode

Mengyang Li^a^,^c,†, Cuibo Liu^a,†, Yi Huang^a, Shuyan Han^a, Bing Zhang^a^,^b^,^*()

^aDepartment of Chemistry, School of Science, Institute of Molecular Plus, Tianjin University, Tianjin 300072, China
^bFrontiers Science Center for Synthetic Biology (Ministry of Education), Tianjin Key Laboratory of Molecular Optoelectronic Sciences Tianjian University, Tianjin 300072, China
^cCollege of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China

Received:2021-02-26 Revised:2021-02-26 Accepted:2021-05-04 Online:2021-11-18 Published:2021-05-18
Contact: Bing Zhang
About author:^*Tel: +86-22-27406140; Fax: +86-22-27403475; E-mail: bzhang@tju.edu.cn
Bing Zhang (Department of Chemistry, School of Science, Tianjin University) received his Ph.D. degree from the University of Science and Technology of China in 2007 (with Prof. Yi Xie). He carried out postdoctoral research at the University of Pennsylvania (July 2007 to July 2008, with Prof. Ritesh Agarwal) and worked as an Alexander von Humboldt fellow at the Max Planck Institute of Colloids and Interfaces (August 2008 to July 2009, with Dayang Wang). Currently, he is a Fellow of the Royal Society of Chemistry (FRSC), a senior member of the Chinese Chemical Society, and a professor at Tianjin University. He mainly focuses on the controlled chemical transformation synthesis of designed targeted nanomaterials for water splitting and water-involved transfer hydrogenation reactions. In 2020, he joined the Editorial Board of the Chinese Journal of Catalysis.First author contact:^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21871206);National Natural Science Foundation of China(22001192)

Abstract

Abstract:

A room-temperature electrochemical strategy for hydrogenation (deuteration) and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode is developed, which includes the hydrogenation of quinoxaline using H₂O as the hydrogen source with 80% Faradaic efficiency and the reverse dehydrogenation of hydrogen-rich 1,2,3,4-tetrahydroquinoxaline with up to 99% yield and selectivity. The in situ generated active hydrogen atom (H*) is plausibly involved in the hydrogenation of quinoxaline, where a consecutive hydrogen radical coupled electron transfer pathway is proposed. Notably, the MoNi₄ alloy exhibits efficient quinoxaline hydrogenation at an overpotential of only 50 mV, owing to its superior water dissociation ability to provide H* in alkaline media. In situ Raman tests indicate that the Ni^II/Ni^III redox couple can promote the dehydrogenation process, representing a promising anodic alternative to low-value oxygen evolution. Impressively, electrocatalytic deuteration is easily achieved with up to 99% deuteration ratios using D₂O. This method is capable of producing a series of functionalized hydrogenated and deuterated quinoxalines.

Key words: Electrocatalysis, Transfer hydrogenation, Deuteration, Water as the hydrogen source, Bifunctional electrode

Mengyang Li, Cuibo Liu, Yi Huang, Shuyan Han, Bing Zhang. Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode[J]. Chinese Journal of Catalysis, 2021, 42(11): 1983-1991.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63834-2

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Figures/Tables 6

Fig. 1. (a) Reported homogeneous and heterogeneous catalytic hydrogenation of N-heteroarenes. (b) Electrocatalytic transfer hydrogenation/deuteration using H2O or D2O and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi4 electrode.

Fig. 2. (a) SEM image of MoNi4 nanosheet arrays. TEM (b,c) and HRTEM (d) images of MoNi4 nanosheets; (e-g) Elemental mapping of MoNi4 nanosheets; (h) XRD patterns of powder scratched from the MoNi4 electrode; (i,j) Ni 2p and Mo 3d XPS profiles for MoNi4 nanosheets.

Fig. 3. (a) LSV curves of MoNi4 cathode at a scan rate of 1 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 1a. (b) Potential-dependent FEs and selectivity of 2a. Conditions: 1a (0.1 mmol), MoNi4 electrode (working area: 1.0 cm2), 1.0 M KOH (7.0 mL), 38.5 C charge transferred, room temperature. (c) Comparison with other electrodes. Conditions: 1a (0.1 mmol), electrode (working area: 1.0 cm2), 1.0 M KOH (7.0 mL), -0.5 V vs. RHE, 38.5 C charge transferred. (d) Time-dependent evolution of 1a, fully and half-hydrogenated products 2a and DHQ. 48 C transferred for the full conversion of 0.1 mmol of 1a. (e) J-t curve of MoNi4 at -0.05 V vs. RHE with intermittent addition of 0.1 mmol of 1a. (f) Cycle-dependent yields and FEs of 2a. 48 C transferred for each cycle. Conv. = Conversion. Sel. = Selectivity.

Fig. 4. (a) LSV curves of glassy carbon cathode at a scan rate of 5 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 1a; (b) Spin trapping of hydrogen radical; (c) Transformations of 1a with and without the addition of t-BuOH; (d) HPLC chromatograms acquired at various electrolysis times; (e) Proposed mechanism.

Fig. 5. Substrate scope of electrocatalytic transfer hydrogenation/deuteration of N-heteroarenes with H2O or D2O over MoNi4 cathode. a Reaction conditions: 1 (0.3 mmol), MoNi4 electrode (working area: 1.0 cm2), 1.0 M KOH (Diox/H2O, 1:6 v/v, 7 mL), room temperature, constant current = 25 mA, 6 h. b 10 h. c 1.0 M K2CO3 (Diox/D2O, 1:6 v/v, 7 mL). Conversion yields of 1 are reported. Numbers in parentheses are the selectivity of 2.

Fig. 6. (a) LSV curves of MoNi4 anode at a scan rate of 5 mV s-1 in 10 mL of 1.0 M KOH with and without 10 mM of 2a; (b) Potential-dependent in situ Raman tests; (c) Time-dependent in situ Raman tests at 1.45 V vs. RHE in 1.0 M KOH solution in the presence of 10 mM of 2a; (d) Proposed process for dehydrogenation of 2a over MoNi4 anode; (e) LSV curves and comparison of potential for achieving benchmark current densities (10 and 20 mA cm-2) over MoNi4 || MoNi4 electrolyzer in 1.0 M KOH with and without 10 mM of 2a.

References

[1]	V. Baliah, R. Jeyaraman, L. Chandrasekaran, Chem. Rev., 1983, 83, 379-423.
[2]	V. Sridharan, P. A. Suryavanshi, J. C. Menéndez, Chem. Rev., 2011, 111, 7157-7259.
[3]	D. S. Wang, Q. A. Chen, S. M. Lu, Y. G. Zhou, Chem. Rev., 2012, 112, 2557-2590.
[4]	Z. Wei, F. Shao, J. Wang, Chin. J. Catal., 2019, 40, 980-1002.
[5]	F. Shao, Z. Yao, Y. Gao, Q. Zhou, Z. Bao, G. Zhuang, X. Zhong, G. Wu, Z. Wei, J. Wang, Chin. J. Catal., 2021, 42, 1185-1194.
[6]	M. Li, C. Liu, B. Zhang, Sci. Bull., 2021, 66, 1047-1049.
[7]	X. F. Cai, W. X. Huang, Z. P. Chen, Y. G. Zhou, Chem. Commun., 2014, 50, 9588-9590.
[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]	J. Wen, R. Tan, S. Liu, Q. Zhao, X. Zhang, Chem. Sci., 2016, 7, 3047-3051.
[10]	R. Yamaguchi, C. Ikeda, Y. Takahashi, K. I. Fujita, J. Am. Chem. Soc., 2009, 131, 8410-8412.
[11]	R. A. Sánchez-Delgado, E. González, Polyhedron, 1989, 8, 1431-1436.
[12]	G. Zhu, K. Pang, G. Parkin, J. Am. Chem. Soc., 2008, 130, 1564-1565.
[13]	V. Papa, Y. Cao, A. Spannenberg, K. Junge, M. Beller, Nat. Catal., 2020, 3, 135-142.
[14]	Y. Gong, P. Zhang, X. Xu, Y. Li, H. Li, Y. Wang, J. Catal., 2013, 297, 272-280.
[15]	H. Mao, J. Ma, Y. Liao, S. Zhao, X. Liao, Catal. Sci. Technol., 2013, 3, 1612-1617.
[16]	D. Ge, L. Hu, J. Wang, X. Li, F. Qi, J. Lu, X. Cao, H. Gu, ChemCatChem, 2013, 5, 2183-2186.
[17]	M. Tang, J. Deng, M. Li, X. Li, H. Li, Z. Chen, Y. Wang, Green Chem., 2016, 18, 6082-6090.
[18]	L. Zhang, X. Wang, Y. Xue, X. Zeng, H. Chen, R. Li, S. Wang, Catal. Sci. Technol., 2014, 4, 1939-1948.
[19]	A. Sánchez, M. Fang, A. Ahmed, R. A. Sánchez-Delgado, R. A, Appl. Catal. A, 2014, 477, 117-124.
[20]	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.
[21]	I. Sorribes, L. Liu, A. Doménech-Carbó, A. Corma, ACS Catal., 2018, 8, 4545-4557.
[22]	N. A. Beckers, S. Huynh, X. Zhang, E. J. Luber, J. M. Buriak, ACS Catal., 2012, 2, 1524-1534.
[23]	S. Zhang, Z. Xia, T. Ni, H. Zhang, C. Wu, Y. Qu, J. Mater. Chem. A, 2017, 5, 3260-3266.
[24]	J. Atzrodt, V. Derdau, W. J. Kerr, M. Reid, Angew. Chem. Int. Ed., 2018, 57, 1758-1784.
[25]	T. G. Gant, J. Med. Chem., 2014, 57, 3595-3611.
[26]	T. D. Nguyen, G. Hukic-Markosian, F. Wang, L. Wojcik, X. G. Li, E. Ehrenfreund, Z. V. Vardeny, Nat. Mater., 2010, 9, 345-352.
[27]	S. Källström, R. Leino, Bioorg. Med. Chem., 2008, 16, 601-635.
[28]	J. D. Scott, R. M. Williams, Chem. Rev., 2002, 102, 1669-1730.
[29]	Y. Jiang, R. Long, Y. Xiong, Chem. Sci., 2019, 10, 7310-7326.
[30]	Y. Wang, W. Zhou, R. Jia, Y. Yu, B. Zhang, Angew. Chem. Int. Ed., 2020, 59, 5350-5354.
[31]	X. H. Chadderdon, D. J. Chadderdon, J. E. Matthiesen, Y. Qiu, J. M. Carraher, J. P. Tessonnier, W. Li, J. Am. Chem. Soc., 2017, 139, 14120-14128.
[32]	S. Han, Y. Shi, C. Wang, C. Liu, B. Zhang, Cell Rep. Phys. Sci., 2021, 2,100337.
[33]	J. Tan, W. Zhang, Y. Shu, H. Lu, Y. Tang, Q. Gao, Sci. Bull., 2021, 66, 1003-1012.
[34]	C. Liu, S. Han, M. Li, X. Chong, B. Zhang, Angew. Chem. Int. Ed., 2020, 59, 18527-18531.
[35]	Y. Wu, C. Liu, C. Wang, S. Lu, B. Zhang, Angew. Chem. Int. Ed., 2020, 59, 21170-21175.
[36]	Y. Zhao, C. Liu, C. Wang, X. Chong, B. Zhang, CCS Chem., 2021, 3, 507-515.
[37]	C. J. Bondue, M. T. M. Koper, J. Am. Chem. Soc., 2019, 141, 12071-12078.
[38]	J. Zhang, T. Wang, P. Liu, Z. Liao, S. Liu, X. Zhuang, M. Chen, E. Zschech, X. Feng, Nat. Commun., 2017, 8, 15437.
[39]	Y. Jin, X. Yue, C. Shu, S. Huang, P. K. Shen, J. Mater. Chem. A, 2017, 5, 2508-2513.
[40]	Q. Zhang, P. Li, D. Zhou, Z. Chang, Y. Kuang, X. Sun, Small, 2017, 13, 1701648.
[41]	Y. Y. Chen, Y. Zhang, X. Zhang, T. Tang, H. Luo, S. Niu, Z. H. Dai, L. J. Wan, J. S. Hu, Adv. Mater., 2017, 29, 1703311.
[42]	E. J. Jacobsen, L. S. Stelzer, K. L. Belonga, D. B. Carter, W. B. Im, V. H. Sethy, A. H. Tang, P. F. VonVoigtlander, J. D. Petke, J. Med. Chem., 1996, 39, 3820-3836.
[43]	S. J. Benkovic, P. A. Benkovic, D. R. Comfort, J. Am. Chem. Soc., 1969, 91, 5270-5279.
[44]	M. P. Mertes, A. J. Lin, J. Med. Chem., 1970, 13, 77-82.
[45]	Y. Ohtake, A. Naito, H. Hasegawa, K. Kawano, D. Morizono, M. Tangiguchi, Y. Tanka, H. Matsukwa, K. Naito, T. Oguma, Y. Ezure, Y. Tsuriya, Bioorg. Med. Chem., 1999, 7, 1247-1254.
[46]	H. X. Lei, K. Zhang, Y.X. Qin, R. J. Dong, D. Z. Chen, H. Zhou, X. H. Sheng, J. Mol. Struct., 2021, 1228, 129485.
[47]	C. T. Eary, Z. S. Jones, R. D. Groneberg, L. E. Burgess, D. A. Mareska, M. D. Drew, J. F. Blake, E. R. Laird, D. Balachari, M. O’sullivan, A. Allen, V. Marsh, Bioorg. Med. Chem. Lett., 2007, 17, 2608-2613.
[48]	J. A. Sikorski, J. Med. Chem., 2006, 49, 1-22.
[49]	R. P. Law, S. J. Atkinson, P. Bamborough, C.-W. Chung, E. H. Demont, L. J. Gordon, M. Lindon, R. K. Prinjha, A. J. B. Watson, D. J. Hirst, J. Med. Chem., 2018, 61, 4317-4334.
[50]	Y. Chandrasekaran, G. K. Dutta, B. R. Kanth, S. Patil, Dyes and Pigments, 2009, 83, 162-167.
[51]	V. Satam, R. Rajule, S. Bendre, P. Bineesh, V. Kanetkar, J. Heterocycl. Chem., 2009, 46, 221-225.
[52]	A. Wojcik, R. Nicolaescu, P. V. Kamat, Y. Chandrasekaran, S. Patil, J. Phys. Chem. A, 2010, 114, 2744.
[53]	X. Chen, N. C. Berner, C. Backes, G. S. Duesberg, Angew. Chem. Int. Ed., 2016, 55, 5803-5808.
[54]	X. Chen, C. McGlynn, A. R. McDonald, Chem. Mater., 2018, 30, 6978-6982.
[55]	J. V. Lauritsen, J. Kibsgaard, G. H. Olesen, P. G. Moses, B. Hinnemann, S. Helveg, J. K. Nørskov, B. S. Clausen, H. Topsøe, E. Lægsgaard, F. Besenbacher, J. Catal., 2007, 249, 220-233.
[56]	F. Bataille, J. L. Lemberton, P. Michaud, G. Pérot, M. Vrinat, M. Lemaire, E. Schulz, M. Breysse, S. Kasztelan, J. Catal., 2000, 191, 409-422.
[57]	S. Barwe, J. Weidner, S. Cychy, D. M. Morales, S. Dieckhofer, D. Hiltrop, J. Masa, M. Muhler, W. Schuhmann, Angew. Chem. Int. Ed., 2018, 57, 11460-11464.
[58]	Y. Huang, X. Chong, C. Liu, Y. Liang, B. Zhang, Angew. Chem. Int. Ed., 2018, 57, 13163-13166.
[59]	C. Huang, Y. Huang, C. Liu, Y. Yu, B. Zhang, Angew. Chem. Int. Ed., 2019, 58, 12014-12017.
[60]	W. Chen, C. Xie, Y. Wang, Y. Zou, C. L. Dong, Y. C. Huang, Z. Xiao, Z. Wei, S. Du, C. Chen, B. Zhou, J. Ma, S. Wang, Chem, 2020, 6, 2974-2993.
[61]	S. Peng, L. Li, H. B. Wu, S. Madhavi, X. W. Lou, Adv. Energy. Mater., 2015, 5, 1401172.
[62]	P. Wang, Z. Yang, Z. Wang, C. Xu, L. Huang, S. Wang, H. Zhang, A. Lei, Angew. Chem. Int. Ed., 2019, 58, 15747-15751.
[63]	Y. Wu, H. Yi, A. Lei, ACS Catal., 2018, 8, 1192-1196.
[64]	P. Xiong, H. C. Xu, Acc. Chem. Res., 2019, 52, 3339-3350.
[65]	Y. Jiang, K. Xu, C. Zeng, Chem. Rev., 2018, 118, 4485-4540.
[66]	H. Liu, J. Han, J. Yuan, C. Liu, D. Wang, T. Liu, M. Liu, J. Luo, A. Wang, J. C. Crittenden, Environ. Sci. Technol., 2019, 53, 11932-11940.
[67]	J. Li, G. Zhan, J. Yang, F. Quan, C. Mao, Y. Liu, B. Wang, F. Lei, L. Li, A. W. M. Chan, L. Xu, Y. Shi, Y. Du, W. Hao, P. K. Wong, J. Wang, S. X. Dou, L. Zhang, J. C. Yu, J. Am. Chem. Soc., 2020, 142, 7036-7046.
[68]	Y. Y. Loh, K. Nagao, A. J. Hoover, D. Hesk, N. R. Rivera, S. L. Colletti, I. W. Davies, D. W. C. MacMillan, Science, 2017, 358, 1182-1187.
[69]	C. Liu, Z. Chen, C. Su, X. Zhao, Q. Gao, G. H. Ning, H. Zhu, W. Tang, K. Leng, W. Fu, B. Tian, X. Peng, J. Li, Q. H. Xu, W. Zhou, K. P. Loh, Nat. Commun., 2018, 9, 80.
[70]	X. Liu, R. Liu, J. Qiu, X. Cheng, G. Li, Angew. Chem. Int. Ed., 2020, 59, 13962-13967.
[71]	C. Q. Zhao, Y. G. Chen, H. Qiu, L. Wei, P. Fang, T. S. Mei, Org. Lett., 2019, 21, 1412-1416.
[72]	P. Zhang, X. Sheng, X. Chen, Z. Fang, J. Jiang, M. Wang, F. Li, L. Fan, Y. Ren, B. Zhang, B. J. J. Timmer, M. S. G. Ahlquist, L. Sun, Angew. Chem. Int. Ed., 2019, 58, 9155-9159.
[73]	B. You, N. Jiang, X. Liu, Y. Sun, Angew. Chem. Int. Ed., 2016, 55, 9913-9917.
[74]	Y. Shi, M. Li, Y. Yu, B. Zhang, Energy Environ. Sci., 2020, 13, 4564-4582.

Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode

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