Citation: Ying Lv, Bing Wang, Haizhu Yu. Mechanism of the Ir/Pd catalyzed photocarboxylation of aryl halides[J]. Chinese Chemical Letters, ;2021, 32(4): 1403-1406. doi: 10.1016/j.cclet.2020.09.045 shu

Mechanism of the Ir/Pd catalyzed photocarboxylation of aryl halides

Ying Lv ^a ,
Bing Wang ^{b, *,} ,
Haizhu Yu ^{a, *,}

a.
Department of Chemistry and Centre for Atomic Engineering of Advanced Materials, Anhui University, Hefei 230601, China
b.
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

ice123wb@mail.ustc.edu.cn

yuhaizhu@ahu.edu.cn

Received Date: 18 August 2020
Revised Date: 15 September 2020
Accepted Date: 24 September 2020
Available Online: 25 September 2020

Figures(9)

The recent Ir/Pd co-catalyzed photo carboxylation of aromatic halides with CO₂ has shown high efficiency and excellent functional group tolerance for preparing aromatic carboxylic acids and esters. With the aid of density functional theory (DFT) calculations, the carboxylation starts with two parallel steps, i.e., oxidative addition of aromatic halides on Pd⁰ and reductive quenching of the photocatalyst Ir(ppy)₂(dtbpy)⁺ with amine. Thereafter, a successive oxidation of Pd^Ⅱ with the amine radical (generated by the reaction of cationic radical amine and Cs₂CO₃) and Ir^Ⅱ species occurs to generate Pd⁰, from which the carboxylation occurs easily via a coordination, Pd-C insertion step. The release of the carboxylate product then regenerates the catalyst.
- Carboxylation,
- Pd-catalysis,
- DFT,
- Charge state,
- Mechanism
1. [1]
  K. Huang, C.L. Sun, Z.J. Shi, Chem. Soc. Rev. 40(2011) 2435-2452. doi: 10.1039/c0cs00129e
2. [2]
  M. Cokoja, C. Bruckmeier, B. Rieger, et al., Angew. Chem. Int. Ed. 50(2011) 8510-8537. doi: 10.1002/anie.201102010
3. [3]
  Y. Tsuji, T. Fujihara, Chem. Commun. 48(2012) 9956-9964. doi: 10.1039/c2cc33848c
4. [4]
  I. Omae, Coord. Chem. Rev. 256(2012) 1384-1405. doi: 10.1016/j.ccr.2012.03.017
5. [5]
  C. Maeda, Y. Miyazaki, T. Ema, Catal. Sci. Technol. 4(2014) 1482-1497. doi: 10.1039/c3cy00993a
6. [6]
  C.S. Yeung, V.M. Dong, Top. Catal. 57(2014) 1342-1350. doi: 10.1007/s11244-014-0301-9
7. [7]
  D. Yu, S.P. Teong, Y. Zhang, Coord. Chem. Rev. 293-294(2015) 279-291.
8. [8]
  Q. Liu, L. Wu, R. Jackstell, et al., Nat. Commun. 6(2015) 5933. doi: 10.1038/ncomms6933
9. [9]
  A. Tortajada, F. Juliá-Hernández, M. Börjesson, et al., Angew. Chem. Int. Ed. 57(2018) 15948-15982. doi: 10.1002/anie.201803186
10. [10]
  Y. Yang, J.W. Lee, Chem. Sci. 10(2019) 3905-3926. doi: 10.1039/C8SC05539D
11. [11]
  L. Song, D.M. Fu, L. Chen, et al., Angew. Chem. Int. Ed 59(2020) 21121-21128. doi: 10.1002/anie.202008630
12. [12]
  X.W. Chen, L. Zhu, Y.Y. Gui, et al., J. Am. Chem. Soc. 141(2019) 18825-18835. doi: 10.1021/jacs.9b09721
13. [13]
  G. Courtois, L. Miginiac, J. Organomet. Chem. 69(1974) 1-44. doi: 10.1016/S0022-328X(00)92983-8
14. [14]
  A.S. Hussey, J. Am. Chem. Soc. 73(1951) 1364-1365.
15. [15]
  Y.J. Zhou, M. Xiao, S.J. Wang, et al., Chin. Chem. Lett. 24(2013) 307-310. doi: 10.1016/j.cclet.2013.02.001
16. [16]
  S. Xie, X. Gao, F. Zhou, et al., Chin. Chem. Lett. 31(2020) 324-328. doi: 10.1016/j.cclet.2019.05.060
17. [17]
  S.S. Yan, Q. Fu, L.L. Liao, et al., Coor. Chem. Rev. 374(2018) 439-463. doi: 10.1016/j.ccr.2018.07.011
18. [18]
  A. Tortajada, F. Juliá-Hernández, M. Börjesson, et al., Angew. Chem. Int. Ed. 57(2018) 15948-15982. doi: 10.1002/anie.201803186
19. [19]
  C.S. Yeung, Angew. Chem. Int. Ed. 58(2019) 5492-5502. doi: 10.1002/anie.201806285
20. [20]
  M. Shi, K.M. Nicholas, J. Am. Chem. Soc. 119(1997) 5057-5058. doi: 10.1021/ja9639832
21. [21]
  J. Wu, N. Hazari, Chem. Commun. 47(2010) 1069-1071.
22. [22]
  D.P. Hruszkewycz, J. Wu, N. Hazari, et al., J. Am. Chem. Soc. 133(2011) 3280-3283. doi: 10.1021/ja110708k
23. [23]
  X. Feng, A. Sun, S. Zhang, et al., Org. Lett. 15(2013) 108-111. doi: 10.1021/ol303135e
24. [24]
  C.S. Yeung, V.M. Dong, J. Am. Chem. Soc. 130(2008) 7826-7827. doi: 10.1021/ja803435w
25. [25]
  H. Ochiai, M. Jang, K. Hirano, et al., Org. Lett. 10(2008) 2681-2683. doi: 10.1021/ol800764u
26. [26]
  K. Ukai, M. Aoki, J. Takaya, et al., J. Am. Chem. Soc. 128(2006) 8706-8707. doi: 10.1021/ja061232m
27. [27]
  J. Takaya, S. Tadami, K. Ukai, et al., Org. Lett. 10(2008) 2697-2700. doi: 10.1021/ol800829q
28. [28]
  T. Ohishi, M. Nishiura, Z. Hou, Angew. Chem. Int. Ed. 47(2008) 5792-5795. doi: 10.1002/anie.200801857
29. [29]
  T. Ohishi, L. Zhang, M. Nishiura, et al., Angew. Chem. Int. Ed. 50(2011) 8114-8117. doi: 10.1002/anie.201101769
30. [30]
  W. Wang, G. Zhang, R. Lang, et al., Green Chem. 15(2013) 635-640. doi: 10.1039/c3gc36830k
31. [31]
  H.A. Duong, P.B. Huleatt, Q. -W. Tan, et al., Org. Lett. 15(2013) 4034-4037. doi: 10.1021/ol4019375
32. [32]
  Y. Makida, E. Marelli, A.M.Z. Slawin, et al., Chem. Commun. 50(2014) 8010-8013. doi: 10.1039/c4cc03650f
33. [33]
  A. Correa, R. Martín, J. Am. Chem. Soc. 131(2009) 15974-15975. doi: 10.1021/ja905264a
34. [34]
  T. Fujihara, K. Nogi, T. Xu, et al., J. Am. Chem. Soc. 134(2012) 9106-9109. doi: 10.1021/ja303514b
35. [35]
  T. León, A. Correa, R. Martin, J. Am. Chem. Soc. 135(2013) 1221-1224. doi: 10.1021/ja311045f
36. [36]
  H. Tran-Vu, O. Daugulis, ACS Catal. 3(2013) 2417-2420. doi: 10.1021/cs400443p
37. [37]
  K. Shimomaki, K. Murata, R. Martin, et al., J. Am. Chem. Soc. 139(2017) 9467-9470. doi: 10.1021/jacs.7b04838
38. [38]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 16, Revision A. 01, Gaussian Inc., Wallingford CT, 2016.
39. [39]
  A.D. Becke, Phys. Rev. A 38(1988) 3098-3100. doi: 10.1103/PhysRevA.38.3098
40. [40]
  C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37(1988) 785-789. doi: 10.1103/PhysRevB.37.785
41. [41]
  D. Andrae, U. Häußermann, M. Dolg, et al., Theor. Chim. Acta 77(1990) 123-141. doi: 10.1007/BF01114537
42. [42]
  F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 7(2005) 3297-3305. doi: 10.1039/b508541a
43. [43]
  S. Grimme, S.L. Ehrlich, J. Comput. Chem. 32(2011) 1456-1465. doi: 10.1002/jcc.21759
44. [44]
  A.V. Marenich, C.J. Cramer, D.G. Truhlar, J. Phys. Chem. B 113(2009) 6378-6396. doi: 10.1021/jp810292n
45. [45]
  A.E. Reed, R.B. Weinstock, F. Weinhold, J. Chem. Phys. 83(1985) 735-746. doi: 10.1063/1.449486
46. [46]
  C.Y. Legault, CYLview, Version 1.0B, (2009), . http://www.cylview.org/.
47. [47]
  M.H. Shaw, J. Twilton, D.W.C. MacMillan, J. Org. Chem. 81(2016) 6898-6926. doi: 10.1021/acs.joc.6b01449
48. [48]
  M.D. Levin, S. Kim, F.D. Toste, ACS Cent. Sci. 2(2016) 293-301. doi: 10.1021/acscentsci.6b00090
49. [49]
  L. Buzzetti, G.E.M. Crisenza, P. Melchiorre, Angew. Chem. Int. Ed. 58(2019) 3730-3747.
50. [50]
  J.D. Slinker, A.A. Gorodetsky, M.S. Lowry, et al., J. Am. Chem. Soc. 126(2004) 2763-2767. doi: 10.1021/ja0345221
51. [51]
  D.H. Gibson, Coord. Chem. Rev. 185-186(1999) 335-355.
1. [1]
  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
2. [2]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
3. [3]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
4. [4]
  Tsegaye Tadesse Tsega , Jiantao Zai , Chin Wei Lai , Xin-Hao Li , Xuefeng Qian . Earth-abundant CuFeS2 nanocrystals@graphite felt electrode for high performance aqueous polysulfide/iodide redox flow batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100192-100192. doi: 10.1016/j.cjsc.2024.100192
5. [5]
  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
6. [6]
  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
7. [7]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
13. [13]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
14. [14]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
15. [15]
  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
16. [16]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
17. [17]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
18. [18]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
19. [19]
  Linhui Liu , Wuwan Xiong , Mingli Fu , Junliang Wu , Zhenguo Li , Daiqi Ye , Peirong Chen . Efficient NO_x abatement by passive adsorption over a Pd-SAPO-34 catalyst prepared by solid-state ion exchange. Chinese Chemical Letters, 2024, 35(4): 108870-. doi: 10.1016/j.cclet.2023.108870
20. [20]
  Bharathi Natarajan , Palanisamy Kannan , Longhua Guo . Metallic nanoparticles for visual sensing: Design, mechanism, and application. Chinese Journal of Structural Chemistry, 2024, 43(9): 100349-100349. doi: 10.1016/j.cjsc.2024.100349

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(571)
HTML views(74)

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