Plasmon-Mediated Organic Photoelectrochemistry Applied to Amination Reactions.
C−H activation
amination
organic electrocatalysis
plasmon-assisted chemistry
regio-selectivity
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
15 May 2024
15 May 2024
Historique:
revised:
08
04
2024
received:
09
01
2024
medline:
15
5
2024
pubmed:
15
5
2024
entrez:
15
5
2024
Statut:
aheadofprint
Résumé
Organic electrochemistry is currently experiencing an era of renaissance, which is closely related to the possibility of carrying out organic transformations under mild conditions, with high selectivity, high yields, and without the use of toxic solvents. Combination of organic electrochemistry with alternative approaches, such as photo-chemistry was found to have great potential due to induced synergy effects. In this work, we propose for the first time utilization of plasmon triggering of enhanced and regio-controlled organic chemical transformation performed in photoelectrochemical regime. The advantages of the proposed route is demonstrated in the model amination reaction with formation of C-N bond between pyrazole and substituted benzene derivatives. Amination was performed in photo-electrochemical mode on the surface of plasmon active Au@Pt electrode with attention focused on the impact of plasmon triggering on the reaction efficiency and regio-selectivity. The ability to enhance the reaction rate significantly and to tune products regio-selectivity is demonstrated. We also performed density functional theory calculations to inquire about the reaction mechanism and potentially explain the plasmon contribution to electrochemical reaction rate and regioselectivity.
Identifiants
pubmed: 38747893
doi: 10.1002/cplu.202400020
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202400020Subventions
Organisme : GACR
ID : 23-08509S
Organisme : NWO Domain Science
Informations de copyright
© 2024 The Authors. ChemPlusChem published by Wiley-VCH GmbH.
Références
H. Kolbe, J. Prakt. Chem. 1847, 41, 137–139.
M. Faraday, Ann. Phys. 1834, 109, 481–520.
C. Zhu, N. W. J. Ang, T. H. Meyer, Y. Qiu, L. Ackermann, ACS Cent. Sci. 2021, 7, 415–431.
M. Yan, Y. Kawamata, P. S. Baran, Chem. Rev. 2017, 117, 13230–13319.
K. Mahanty, S. Kumar Saha, A. Halder, S. D. Sarkar, Chem. Commun. 2023, 59, 4467–4470.
X. Hu, I. Cheng-Sánchez, S. Cuesta-Galisteo, C. Nevado, J. Am. Chem. Soc. 2023, 145, 6270–6279.
C. Ma, P. Fang, Z.-R. Liu, S.-S. Xu, K. Xu, X. Cheng, A. Lei, H.-C. Xu, C. Zeng, T.-S. Mei, Sci. Bull. 2021, 66, 2412–2429.
N. E. S. Tay, D. Lehnherr, T. Rovis, Chem. Rev. 2022, 122, 2487–2649.
Y. Yu, P. Guo, J.-S. Zhong, Y. Yuan, K.-Y. Ye, Org. Chem. Front. 2020, 7, 131–135.
H. Kim, H. Kim, T. H. Lambert, S. Lin, J. Am. Chem. Soc. 2020, 142, 2087–2092.
Y. Yuan, J. Yang, J. Zhang, Chem. Sci. 2023, 14, 705–710.
T. Shen, Y.-L. Li, K.-Y. Ye, T. H. Lambert, Nature 2023, 614, 275–280.
J. Liu, C. Xia, S. Zaman, Y. Su, L. Tan, S. Chen, J. Mater. Chem. A 2023, 11, 16918–16932.
W. Zhang, K. L. Carpenter, S. Lin, Angew. Chem. 2020, 132, 417–425.
H. Yan, Z. Hou, H. Xu, Angew. Chem. Int. Ed. 2019, 58, 4592–4595.
H. Huang, Z. M. Strater, M. Rauch, J. Shee, T. J. Sisto, C. Nuckolls, T. H. Lambert, Angew. Chem. Int. Ed. 2019, 58, 13318–13322.
L. Zhang, L. Liardet, J. Luo, D. Ren, M. Grätzel, X. Hu, Nat. Catal. 2019, 2, 366–373.
P. Subramanyam, B. Meena, V. Biju, H. Misawa, S. Challapalli, J. Photochem. Photobiol. C 2022, 51, 100472.
A. Zabelina, J. Dedek, O. Guselnikova, D. Zabelin, A. Trelin, E. Miliutina, Z. Kolska, J. Siegel, V. Svorcik, J. Vana, O. Lyutakov, ACS Catal. 2023, 13, 3830–3840.
S. Wang, Y. Zhang, Y. Zheng, Y. Xu, G. Yang, S. Zhong, Y. Zhao, S. Bai, Small 2023, 19, 2204774.
A. Zabelina, E. Miliutina, D. Zabelin, V. Burtsev, V. Buravets, R. Elashnikov, V. Neubertova, M. Šťastný, D. Popelková, J. Lancok, S. Chertopalov, M. Paidar, A. Trelin, A. Michalcová, V. Švorčík, O. Lyutakov, J. Chem. Eng. 2023, 454, 140441.
H. Wang, C. Cheng, K. Du, Z. Xu, E. Zhao, N. Lan, P.-F. Yin, T. Ling, Chem. Eur. J. 2023, 29, e202300204.
M. Duca, M. T. M. Koper, in Surface and Interface Science (Ed.: K. Wandelt), Wiley, 2020, pp. 773–890.
Z. Zhang, C. Zhang, H. Zheng, H. Xu, Acc. Chem. Res. 2019, 52, 2506–2515.
E. Kazuma, Y. Kim, Angew. Chem. Int. Ed. 2019, 58, 4800–4808.
L. Mascaretti, A. Dutta, Š. Kment, V. M. Shalaev, A. Boltasseva, R. Zbořil, A. Naldoni, Adv. Mater. 2019, 31, 1805513.
O. Guselnikova, P. Postnikov, M. M. Chehimi, Y. Kalachyovaa, V. Svorcik, O. Lyutakov, Langmuir 2019, 35, 2023–2032.
Q. Wang, K. Domen, Chem. Rev. 2020, 120, 919–985.
N. P. de Leon, B. J. Shields, C. L. Yu, D. E. Englund, A. V. Akimov, M. D. Lukin, H. Park, Phys. Rev. Lett. 2012, 108, 226803.
L. Wang, M. Hasanzadeh Kafshgari, M. Meunier, Adv. Funct. Mater. 2020, 30, 2005400.
S. Li, P. Miao, Y. Zhang, J. Wu, B. Zhang, Y. Du, X. Han, J. Sun, P. Xu, Adv. Mater. 2021, 33, 2000086.
O. Guselnikova, A. Olshtrem, Y. Kalachyova, I. Panov, P. Postnikov, V. Svorcik, O. Lyutakov, J. Phys. Chem. C 2018, 122, 26613–26622.
M. Tahir, M. Siraj, B. Tahir, M. Umer, H. Alias, N. Othman, Appl. Surf. Sci. 2020, 503, 144344.
S. Linic, S. Chavez, R. Elias, Nat. Mater. 2021, 20, 916–924.
D. B. Ingram, S. Linic, J. Am. Chem. Soc. 2011, 133, 5202–5205.
J. Liu, C. Xia, S. Zaman, Y. Su, L. Tan, S. Chen, J. Mater. Chem. A 2023, 11, 16918–16932.
M. Ali, F. Zhou, K. Chen, C. Kotzur, C. Xiao, L. Bourgeois, X. Zhang, D. R. MacFarlane, Nat. Commun. 2016, 7, 11335.
S. Chen, W.-H. Li, W. Jiang, J. Yang, J. Zhu, L. Wang, H. Ou, Z. Zhuang, M. Chen, X. Sun, D. Wang, Y. Li, Angew. Chem. Int. Ed. 2022, 61, e202114450.
S. Chen, Z. Zhang, W. Jiang, S. Zhang, J. Zhu, L. Wang, H. Ou, S. Zaman, L. Tan, P. Zhu, E. Zhang, P. Jiang, Y. Su, D. Wang, Y. Li, J. Am. Chem. Soc. 2022, 144, 12807–12815.
Z. Zhang, C. Zhang, H. Zheng, H. Xu, Acc. Chem. Res. 2019, 52, 2506–2515.
F. Chen, Q. Yang, C. Niu, X. Li, C. Zhang, G. Zeng, RSC Adv. 2015, 5, 63152–63164.
B. Mondal, P. S. Mukherjee, J. Am. Chem. Soc. 2018, 140, 12592–12601.
F. Wang, C. Li, H. Chen, R. Jiang, L.-D. Sun, Q. Li, J. Wang, J. C. Yu, C.-H. Yan, J. Am. Chem. Soc. 2013, 135, 5588–5601.
H. L. Luk, J. Feist, J. J. Toppari, G. Groenhof, J. Chem. Theory Comput. 2017, 13, 4324–4335.
A. Ricci, Amino Group Chemistry: From Synthesis to the Life Sciences, Wiley-VCH, Weinheim, 2008.
Y. Kalachyova, O. Lyutakov, P. Slepicka, R. Elashnikov, V. Svorcik, Nanoscale Res. Lett. 2014, 9, 591.
V. Sukowski, M. van Borselen, S. Mathew, M. Á. Fernández-Ibáñez, Angew. Chem. Int. Ed. 2022, 61, e202201750.
N. A. Romero, K. A. Margrey, N. E. Tay, D. A. Nicewicz, Science 2015, 349, 1326–1330.
K. A. Margrey, J. B. McManus, S. Bonazzi, F. Zecri, D. A. Nicewicz, J. Am. Chem. Soc. 2017, 139, 11288–11299.
L. Niu, H. Yi, S. Wang, T. Liu, J. Liu, A. Lei, Nat. Commun. 2017, 8, 14226.
P. A. Kempler, A. C. Nielander, Nat. Commun. 2023, 14, 1158.
R. Réocreux, C. A. Ould Hamou, C. Michel, J. B. Giorgi, P. Sautet, ACS Catal. 2016, 6, 8166–8178.
N. Bonalumi, A. Vargas, D. Ferri, A. Baiker, J. Phys. Chem. B 2006, 110, 9956–9965.
A. Bard, Standard Potentials in Aqueous Solution, Routledge, 2017.
O. Diaz-Morales, T. J. P. Hersbach, C. Badan, A. C. Garcia, M. T. M. Koper, Faraday Discuss. 2018, 210, 301–315.
F. Neese, WIREs Comput. Mol. Sci. 2022, 12, e1606.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378–6396.
G. Henkelman, B. P. Uberuaga, H. Jónsson, J. Chem. Phys. 2000, 113, 9901–9904.
T. D. Kühne, M. Iannuzzi, M. Del Ben, V. V. Rybkin, P. Seewald, F. Stein, T. Laino, R. Z. Khaliullin, O. Schütt, F. Schiffmann, D. Golze, J. Wilhelm, S. Chulkov, M. H. Bani-Hashemian, V. Weber, U. Borštnik, M. Taillefumier, A. S. Jakobovits, A. Lazzaro, H. Pabst, T. Müller, R. Schade, M. Guidon, S. Andermatt, N. Holmberg, G. K. Schenter, A. Hehn, A. Bussy, F. Belleflamme, G. Tabacchi, A. Glöß, M. Lass, I. Bethune, C. J. Mundy, C. Plessl, M. Watkins, J. VandeVondele, M. Krack, J. Hutter, J. Chem. Phys. 2020, 152, 194103.
S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456–1465.
S. Goedecker, M. Teter, J. Hutter, Phys. Rev. B 1996, 54, 1703–1710.
J. VandeVondele, J. Hutter, J. Chem. Phys. 2007, 127, 114105.
B. G. Lippert, J. H. Parrinello, M. Parrinello, Mol. Phys. 1997, 92, 477–488.
R. Kronberg, K. Laasonen, ACS Catal. 2021, 11, 8062–8078.
H. B. Michaelson, J. Appl. Phys. 2008, 48, 4729–4733.