Citation: Lingling Liu, Hongli Wu, Genping Huang. Mechanism and selectivity of nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones: A computational study[J]. Chinese Chemical Letters, ;2021, 32(10): 3015-3018. doi: 10.1016/j.cclet.2021.04.006 shu

Mechanism and selectivity of nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones: A computational study

Department of Chemistry, School of Science and Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072, China

gphuang@tju.edu.cn

Received Date: 25 February 2021
Revised Date: 31 March 2021
Accepted Date: 1 April 2021
Available Online: 3 April 2021

Figures(5)

Density functional theory calculations have been performed to investigate the nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones. The computations show that the overall catalytic cycle consists of four major steps, including: (1) C-C oxidative addition of the cyclopropenone to afford the four-membered nickelacycle, (2) isomerization, (3) migratory insertion via a 4, 1-insertion fashion, and (4) C-C reductive elimination to deliver the [3 + 2] cycloaddition product. The enantioselectivity is mainly attributed to the π-π interaction between the diphenylcyclopropenone moiety and the phenyl substituent of the oxazoline ring of the ligand. The chemoselectivity of the C = O versus C = C insertion was rationalized in terms of the steric effect.
- Nickel catalyst,
- Cycloaddition,
- Mechanism,
- Selectivity,
- DFT calculations
1. [1]
  (a) R. Peng, Y. Xu, Q. Cao, Chin. Chem. Lett. 29 (2018) 1465-1474;
  (b) L. Wang, Z. Yu, Chin. J. Org. Chem. 40 (2020) 3536-3558;
  (c) A. Roglans, A. Pla-Quintana, M. Sola, Chem. Rev. 121 (2021) 1894-1979;
  (d) J. Wang, S.A. Blaszczyk, X. Li, et al., Chem. Rev. 121 (2021) 110-139.
2. [2]
  (a) P. Chen, B.A. Billett, T. Tsukamoto, et al., ACS Catal. 7 (2017) 1340-1360;
  (b) R. Vicente, Chem. Rev. 121 (2021) 162-226;
  (c) M. Murakami, N. Ishida, Chem. Rev. 121 (2021) 264-299.
3. [3]
  (a) M. Murakami, S. Ashida, T. Matsuda, J. Am. Chem. Soc. 127 (2005) 6932-6933;
  (b) A. Schuster-Haberhauer, R. Gleiter, O. Körner, Organometallics 27 (2008) 1361-1366;
  (c) P. Chen, T. Xu, G. Dong, Angew. Chem. Int. Ed. 53 (2014) 1674-1678;
  (d) P. Chen, J. Sieber, C.H. Senanayake, et al., Chem. Sci. 6 (2015) 5440-5445;
  (e) T. Kondo, Y. Kaneko, Y. Taguchi, et al., J. Am. Chem. Soc. 124 (2002) 6824-6825;
  (f) T. Lin, C. Zhu, P. Zhang, et al., Angew. Chem. Int. Ed. 55 (2016) 10844-10848;
  (g) Q. Li, G. Jiang, L. Jiao, et al., Org. Lett. 12 (2010) 1332-1335.
4. [4]
  D. Bai, Y. Yu, H. Guo, et al., Angew. Chem. Int. Ed. 59(2020) 2740-2744.
5. [5]
  (a) B. Mao, M. Fañanas-Mastral, B.L. Feringa, Chem. Rev. 117 (2017) 10502-10566;
  (b) S. Wang, Y. Liu, N. Cramer, Angew. Chem. Int. Ed. 58 (2019) 18136-18140;
  (c) J. Ji, L. Lin, Q. Tang, et al., ACS Catal. 7 (2017) 3763-3767;
  (d) G.L. Hamilton, E.J. Kang, M. Mba, et al., Science 317 (2007) 496-499.
6. [6]
  (a) Y. Li, Z. Lin, Organometallics 32 (2013) 3003-3011;
  (b) X. Hong, D. Holte, D.C.G. Götz, et al., J. Org. Chem. 79 (2014) 12177-12184;
  (c) Y. Liu, Y. Tang, Y. Jiang, et al., ACS Catal. 7 (2017) 1886-1896;
  (d) S. Yang, Y. Xu, J. Li, Org. Lett. 18 (2016) 6244-6247;
  (e) Y. Luo, C. Shan, Song Liu, et al., ACS Catal. 9 (2019) 10876-10886;
  (f) I. Nohira, S. Liu, R. Bai, et al., J. Am. Chem. Soc. 142 (2020) 17306-17311;
  (g) Y. Li, Y. Luo, L. Peng, et al., Nat. Commun. 11 (2020) 1-13.
7. [7]
  (a) Z. Zhang, J. Zhang, F.K. Sheong, et al., ACS Catal. 10 (2020) 12454-12465;
  (b) J. Guo, H. Wang, S. Xing, et al., Chem 5 (2019) 1-15;
  (c) M. Yuan, Z. Song, S.O. Badir, et al., J. Am. Chem. Soc. 142 (2020) 7225-7234;
  (d) L. Hu, H. Chen, J. Am. Chem. Soc. 139 (2017) 15564-15567;
  (e) Y. Yu, G. Luo, J. Yang, Catal. Sci. Technol. 9 (2019) 1879-1890;
  (f) L. Lin, C. Daia, J. Zhu, Org. Chem. Front. 8 (2021) 1531-1543;
  (g) S. Li, Y. Lan, Chem. Commun. 56 (2020) 6609-6619.
8. [8]
  Y. Luo, C. Shan, S. Liu, ACS Catal. 9(2019) 10876-10886.
9. [9]
  H. Zou, Z. Wang, G. Huang, Chem. Eur. J. 23(2017) 12593-12603.
10. [10]
  (a) L. Xu, Q. Zhu, G. Huang, B. Cheng, Y. Xia, J. Org. Chem. 77 (2012) 3017-3024;
  (b) W. Guo, Y. Xia, J. Org, Chem. 80 (2015) 8113-8121;
  (c) W. Guo, T. Zhou, Y. Xia, Organometallics 34 (2015) 3012-3020;
  (d) L. Xu, X. Zhang, M.S. McCammant, et al., J. Org. Chem. 81 (2016) 7604-7611;
  (e) Y. Liu, Y. Tang, Y.Y. Jiang, et al., ACS Catal. 7 (2017) 1886-1896;
  (f) G. Lu, R.Y. Liu, Y. Yang, et al., J. Am. Chem. Soc. 139 (2017) 16548-16555;
  (g) X. Lv, F. Huang, Y.B. Wu, G. Lu, Catal. Sci. Technol. 8 (2018) 2835-2840;
  (h) X.W. Chen, L. Zhu, Y.Y. Gui, et al., J. Am. Chem. Soc. 141 (2019) 18825-18835;
  (i) X. Li, X. Ren, H. Wu, et al., Chin. Chem. Lett. 32 (2021) 9-12;
  (j) H. Zou, Z.L. Wang, Y. Cao, G. Huang, Chin. Chem. Lett. 29 (2018) 1355-1358;
  (k) X. Li, H. Wu, Z. Wu, G. Huang, J. Org. Chem. 84 (2019) 5514-5523;
  (l) G. Huang, P. Liu, ACS Catal. 6 (2016) 809-820;
  (m) M. Zhang, G. Huang, Dalton Trans. 45 (2016) 3552-3557;
  (n) L. Hu, Z. Wu, G. Huang, Org. Lett. 20 (2018) 5410-5413.
1. [1]
  Weidan Meng , Yanbo Zhou , Yi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961
2. [2]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
3. [3]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
4. [4]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
5. [5]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
6. [6]
  Jia Fu , Shilong Zhang , Lirong Liang , Chunyu Du , Zhenqiang Ye , Guangming Chen . PEDOT-based thermoelectric composites: Preparation, mechanism and applications. Chinese Chemical Letters, 2024, 35(9): 109804-. doi: 10.1016/j.cclet.2024.109804
7. [7]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
8. [8]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
9. [9]
  Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
10. [10]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
11. [11]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
12. [12]
  Junyi Yu , Yin Cheng , Anhong Cai , Xianfeng Huang , Qingrui Zhang . Synthetic Cu(Ⅲ) from copper plating wastewater for onsite decomplexation of Cu(Ⅱ)- and Ni(Ⅱ)-organic complexes. Chinese Chemical Letters, 2025, 36(2): 110549-. doi: 10.1016/j.cclet.2024.110549
13. [13]
  Shaojie Deng , Peihua Ma , Qinghong Bai , Xin Xiao . The transformation of nor-seco-cucurbit[10]uril to cucurbit[5]uril and cucurbit[8]uril controlled by its own concentration. Chinese Chemical Letters, 2025, 36(2): 109878-. doi: 10.1016/j.cclet.2024.109878
14. [14]
  Ming-Yi Sun , Lu Zhang , Ya Li , Chong-Chen Wang , Peng Wang , Xueying Ren , Xiao-Hong Yi . Recovering Ag⁺ with nano-MOF-303 to form Ag/AgCl/MOF-303 photocatalyst: The role of stored Cl⁻ ions. Chinese Chemical Letters, 2025, 36(2): 110035-. doi: 10.1016/j.cclet.2024.110035
15. [15]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
16. [16]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
17. [17]
  Ming-Zhen Li , Yang Zhang , Kun Li , Ya-Nan Shang , Yi-Zhen Zhang , Yu-Jiao Kan , Zhi-Yang Jiao , Yu-Yuan Han , Xiao-Qiang Cao . In situ regeneration of catalyst for Fenton-like degradation by photogenerated electron transportation: Characterization, performance and mechanism comparison. Chinese Chemical Letters, 2025, 36(1): 109885-. doi: 10.1016/j.cclet.2024.109885
18. [18]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
19. [19]
  Tong Zhou , Liyi Xie , Chuyu Liu , Xiyan Zheng , Bao Li . Between Sobriety and Intoxication: The Fascinating Journey of Sauce-Flavored Latte. University Chemistry, 2024, 39(9): 55-58. doi: 10.12461/PKU.DXHX202312048
20. [20]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(620)
HTML views(32)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142