Electric Field Enhanced Ammoxidation of Aldehydes Using Supported Fe Clusters Under Ambient Oxygen Pressure.
Ammoxidation
Electric Field
Heterogeneous Catalysis
Nitriles
Supported Clusters
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
18 Dec 2023
18 Dec 2023
Historique:
received:
07
09
2023
medline:
6
11
2023
pubmed:
6
11
2023
entrez:
6
11
2023
Statut:
ppublish
Résumé
Heterogeneous catalytic ammoxidation provides an eco-friendly route for the cyanide-free synthesis of nitrile compounds, which are important precursors for synthetic chemistry and pharmaceutical applications. However, in general such a process requires high pressures of molecular oxygen at elevated temperatures to accelerate the oxygen reduction and imine dehydrogenation steps, which is highly risky in practical applications. Here, we report an electric field enhanced ammoxidation system using a supported Fe clusters catalyst (Fe/NC), which enables efficient synthesis of nitriles from the corresponding aldehydes under ambient air pressure at room temperature (RT). A synergistic effect between the external electric field and the Fe/NC catalyst promotes the ammonia activation and the dehydrogenation of the generated imine intermediates and avoids the unwanted backwards reaction to aldehydes. This electric field enhanced ammoxidation system presents high efficiency and selectivity for the conversion of a series of aldehydes under mild conditions with high durability, rendering it an attractive process for the green synthesis of nitriles with fragile functional groups.
Identifiants
pubmed: 37930876
doi: 10.1002/anie.202313313
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202313313Subventions
Organisme : National Natural Science Foundation of China
ID : 21972100
Organisme : National Key R&D Program of China
ID : 2020YFA0406103
Organisme : Project of Innovation and Entrepreneurship of Jiangsu Province
ID : JSSCRC202010539
Organisme : Suzhou Foreign Academician Workstation
ID : SWY2022001
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
J. Kim, H. J. Kim, S. Chang, Angew. Chem. Int. Ed. 2012, 51, 11948-11959;
G. Yan, Y. Zhang, J. Wang, Adv. Synth. Catal. 2017, 359, 4068-4105;
H. Hu, S. Wu, F. Yan, M. Makha, Y. Sun, C.-X. Du, Y. Li, J. Energy Chem. 2022, 70, 542-575.
P. Anbarasan, T. Schareina, M. Beller, Chem. Soc. Rev. 2011, 40, 5049-5067;
R. D. Patil, M. K. Gupta, Adv. Synth. Catal. 2020, 362, 3987-4009.
I. P. Beletskaya, A. S. Sigeev, A. S. Peregudov, P. V. Petrovskii, J. Organomet. Chem. 2004, 689, 3810-3812;
F. Mo, G. Dong, Y. Zhang, J. Wang, Org. Biomol. Chem. 2013, 11, 1582.
Q. Zhang, D. Ma, Synlett 2023, 34, 1395-1398;
J. X. Wu, B. Beck, R. X. Ren, Tetrahedron Lett. 2002, 43, 387-389.
T. Schareina, A. Zapf, M. Beller, Chem. Commun. 2004, 1388-1389;
J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890-2891;
C. Yang, J. M. Williams, Org. Lett. 2004, 6, 2837-2840;
P. Pollak, G. Romeder, F. Hagedorn, H.-P. Gelbke, Ullman's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000, pp. 251-263.
B. Chen, L. Zhang, H. Luo, L. Huang, P. He, G. Xue, H. Liang, W. Dai, JACS Au 2023, 3, 476-487;
E. M. Karp, T. R. Eaton, V. S. Nogué, V. Vorotnikov, M. J. Biddy, E. C. D. Tan, D. G. Brandner, R. M. Cywar, R. Liu, L. P. Manker, W. E. Michener, M. Gilhespy, Z. Skoufa, M. J. Watson, O. S. Fruchey, D. R. Vardon, R. T. Gill, A. D. Bratis, G. T. Beckham, Science 2017, 358, 1307-1310;
S. G. Davey, Nat. Chem. Rev. 2018, 2, 0110.
T. A. Hanna, Coord. Chem. Rev. 2004, 248, 429-440.
D. P. Hansora, Industrial manufacturing process of Acrylonitrile, LAP LAMBERT Academic Publishing, London, 2014, pp. 41-53;
F. Rezaie, V. Pirouzfar, A. Alihosseini, Therm. Sci. Eng. Prog. 2020, 16, 100463.
T. Senthamarai, V. G. Chandrashekhar, N. Rockstroh, J. Rabeah, S. Bartling, R. V. Jagadeesh, M. Beller, Chem 2022, 8, 508-531;
X. Liu, J. Qin, W. Dai, Z. Zhu, P. Zhou, Y. Wang, J. Nie, Y. Yang, Z. Zhang, ACS Catal. 2022, 12, 13300-13311;
T. Yasukawa, X. Yang, S. Kobayashi, J. Org. Chem. 2020, 85, 7543-7548.
R. V. Jagadeesh, H. Junge, M. Beller, Nat. Commun. 2014, 5, 4123.
H. Wang, D. Xu, E. Guan, L. Wang, J. Zhang, C. Wang, S. Wang, H. Xu, X. Meng, B. Yang, B. C. Gates, F.-S. Xiao, ACS Catal. 2020, 10, 6299-6308.
K. Sun, H. Shan, H. Neumann, G. P. Lu, M. Beller, Nat. Commun. 2022, 13, 1848;
H. Luo, S. Tian, H. Liang, H. Wang, S. Gao, W. Dai, Nat. Commun. 2023, 14, 2981;
J. Qin, B. Han, X. Liu, W. Dai, Y. Wang, H. Luo, X. Lu, J. Nie, C. Xian, Z. Zhang, Sci. Adv. 2022, 8, eadd1267.
X. Li, W. Wang, F. Dong, Z. Zhang, L. Han, X. Luo, J. Huang, Z. Feng, Z. Chen, G. Jia, T. Zhang, ACS Catal. 2021, 11, 4739-4769;
Z. Wang, Y. Li, C. Wu, S. C. E. Tsang, Joule 2022, 6, 1798-1825;
Y. Xu, Z. Zhou, M. Zou, Y. Liu, Y. Zheng, Y. Yang, S. Lan, J. Lan, C.-W. Nan, Y.-H. Lin, Mater. Today 2022, 54, 225-246;
J. Zhao, X. Zhang, J. Xu, W. Tang, Z. Lin Wang, F. Ru Fan, Angew. Chem. Int. Ed. 2023, 62, e202300604.
G. Pacchioni, J. R. Lomas, F. Illas, J. Mol. Catal. A 1997, 119, 263-273;
J. Yao, W. Huang, W. Fang, M. Kuang, N. Jia, H. Ren, D. Liu, C. Lv, C. Liu, J. Xu, Q. Yan, Small Methods 2020, 4, 2000494.
C. Biz, M. Fianchini, J. Gracia, ACS Catal. 2021, 11, 14249-14261.
H. Yang, Y. Shen, Z. Xiao, C. Liu, K. Yuan, Y. Ding, Chem. Commun. 2020, 56, 2435-2438;
Q. Chen, C. Fang, Z. Shen, M. Li, Electrochem. Commun. 2016, 64, 51-55;
X. Yang, Z. Fan, Z. Shen, M. Li, Electrochim. Acta 2017, 226, 53-59;
M. T. Bender, K.-S. Choi, JACS Au 2022, 2, 1169-1180.
M. Wang, S. Liu, T. Qian, J. Liu, J. Zhou, H. Ji, J. Xiong, J. Zhong, C. Yan, Nat. Commun. 2019, 10, 341.
W. Liu, L. Zhang, X. Liu, X. Liu, X. Yang, S. Miao, W. Wang, A. Wang, T. Zhang, J. Am. Chem. Soc. 2017, 139, 10790-10798.
W. Zhai, S. Huang, C. Lu, X. Tang, L. Li, B. Huang, T. Hu, K. Yuan, X. Zhuang, Y. Chen, Small 2022, 18, e2107225.
Z. Ma, S. Liu, N. Tang, T. Song, K. Motokura, Z. Shen, Y. Yang, ACS Catal. 2022, 12, 5595-5604.
R. J. LeSuer, C. Buttolph, W. E. Geiger, Anal. Chem. 2004, 76, 6395-6401.
Y. Yoon, B. R. Kim, C. Y. Lee, J. Kim, Asian J. Org. Chem. 2016, 5, 746-749;
K.-K. Sun, J.-L. Sun, G.-P. Lu, C. Cai, Green Chem. 2019, 21, 4334-4340;
A. N. Hashemi, H. Eshghi, K. Lamei, Appl. Organomet. Chem. 2019, 33, e4835;
S. Shang, L. Wang, W. Dai, B. Chen, Y. Lv, S. Gao, Catal. Sci. Technol. 2016, 6, 5746-5753;
M. Hua, J. Song, X. Huang, H. Liu, H. Fan, W. Wang, Z. He, Z. Liu, B. Han, Angew. Chem. Int. Ed. 2021, 60, 21479-21485;
Y. Preger, T. W. Root, S. S. Stahl, ACS Omega 2018, 3, 6091-6096.
J.-F. Soulé, H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 18550-18553;
W. Wang, L. Ma, X. Jiang, H. Wang, Z.-H. He, K. Wang, Y. Yang, Z.-T. Liu, ACS Sustainable Chem. Eng. 2022, 10, 14636-14647.
C. Chen, R. P. Veregin, J. R. Harbour, M. L. Hair, S. L. Issler, J. Tromp, J. Phys. Chem. 1989, 93, 2607-2609;
C. F. Chignell, B. Kalyanaraman, R. H. Sik, R. P. Mason, Photochem. Photobiol. 1981, 34, 147-156.