Citation: JIANG Feng, REN Qing-Hua. Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides[J]. Acta Physico-Chimica Sinica, ;2014, 30(5): 821-828. doi: 10.3866/PKU.WHXB201403241 shu

Reaction Mechanism for the Ni-Catalyzed Reductive Cross-Coupling of Aryl Halides

JIANG Feng ,
REN Qing-Hua

1.
Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, P. R. China

Received Date: 10 December 2013
Available Online: 24 March 2014
Fund Project:

The mechanism of the Ni-catalyzed reductive cross-coupling reaction of bromobenzene (R₁) and methyl 4-bromobenzoate (R₂) to form an unsymmetrical biaryl system has been theoretically investigated using density functional theory calculations. Our results showed that the Ni⁰-catalyzed process was favored over the NiI-catalyzed mechanism. The mechanism for the reaction of the Ni⁰ catalyst initially attacking either R₁ or R₂ was quite similar, where the energy barrier in the gas phase for the rate-limiting step was 70.50 or 49.66 kJ·mol^-1, respectively. The mechanism in the favored Ni⁰-catalyzed reaction involved the following steps: first oxidative addition, reduction, second oxidative addition, reductive elimination, and catalyst regeneration. Our calculated results also indicated that no organometallic reagents were produced in the reaction cycle.
- Density functional theory,
- Nickel catalysis,
- Reductive cross-coupling,
- Reaction mechanism,
- Unsymmetrical biaryl
1. [1]
  
  (1) Torssell, K. B. Natural Product Chemistry: a Mechanistic and Biosynthetic Approach to Secondary Metabolism; JohnWiley & Sons: New Jersey, 1983; pp 401-404.
2. [2]
  (2) Bonesi, S. M.; Fagnoni, M.; Albini, A. Angew. Chem. Int. Edit. 2008, 47, 10022. doi: 10.1002/anie.v47:52
3. [3]
  (3) Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651. doi: 10.1021/cr0505268
4. [4]
  (4) Roncali, J. Chem. Rev. 1992, 92, 711. doi: 10.1021/cr00012a009
5. [5]
  (5) Yang, W. Y.; Ahn, J. H.; Yoo, Y. S.; Oh, N. K.; Lee, M. Nat. Mater. 2005, 4, 399. doi: 10.1038/nmat1373
6. [6]
  (6) Huang, Z.; Lee, H.; Lee, E.; Kang, S. K.; Nam, J. M.; Lee, M. Nat. Commun. 2011, 2, 459. doi: 10.1038/ncomms1465
7. [7]
  (7) Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S.W. J. Med. Chem. 2000, 43, 3443. doi: 10.1021/jm000164q
8. [8]
  (8) Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582. doi: 10.1021/jo9612990
9. [9]
  (9) Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885. doi: 10.1021/jo982135h
10. [10]
  (10) Fagnoni, M.; Mella, M.; Albini, A. Org. Lett. 1999, 1, 1299. doi: 10.1021/ol990982g
11. [11]
  (11) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Sasson, Y. J. Org. Chem. 2000, 65, 3107. doi: 10.1021/jo991868e
12. [12]
  (12) Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. Tetrahedron 2000, 56, 9601. doi: 10.1016/S0040-4020(00)00929-7
13. [13]
  (13) Hassan, J.; Sévignon, M.; zzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. doi: 10.1021/cr000664r
14. [14]
  (14) Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284. doi: 10.1021/jo052300a
15. [15]
  (15) Dankwardt, J.W. Angew. Chem. Int. Edit. 2004, 116, 2482.
16. [16]
  (16) Dankwardt, J.W. J. Organomet. Chem. 2005, 690, 932. doi: 10.1016/j.jorganchem.2004.10.037
17. [17]
  (17) Catellani, M.; Motti, E.; Della Ca, N.; Ferraccioli, R. Eur. J. Org. Chem. 2007, 2007, 4153.
18. [18]
  (18) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem. Int. Edit. 2007, 119, 5455.
19. [19]
  (19) Zhou, Z.; Liu, M.; Wu, X.; Yu, H.; Xu, G.; Xie, Y. Appl. Organomet. Chem. 2013, 27, 562.
20. [20]
  (20) Breitenfeld, J.; Vechorkin, O.; Corminboeuf, C.; Scopelliti, R.; Hu, X. Organometallics 2010, 29, 3686. doi: 10.1021/om1007506
21. [21]
  (21) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. doi: 10.1021/cr100327p
22. [22]
  (22) Amatore, M.; smini, C. Angew. Chem. Int. Edit. 2008, 120, 2119.
23. [23]
  (23) Qian, Q.; Zang, Z.; Wang, S.; Chen, Y.; Lin, K.; ng, H. Synlett 2013, 24, 619. doi: 10.1055/s-00000083
24. [24]
  (24) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B. et al. Gaussian 03, Revision 01; Gaussian Inc.; Wallingford, CT, 2004.
25. [25]
  (25) Becke, A. D. Phys. Rev. A 1988, 38, 3098. doi: 10.1103/PhysRevA.38.3098
26. [26]
  (26) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
27. [27]
  (27) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
28. [28]
  (28) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623. doi: 10.1021/j100096a001
29. [29]
  (29) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. doi: 10.1063/1.438955
30. [30]
  (30) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. doi: 10.1063/1.438980
31. [31]
  (31) Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123. doi: 10.1007/BF01114537
32. [32]
  (32) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669. doi: 10.1002/jcc.10189
33. [33]
  (33) Lin, B. L.; Liu, L.; Fu, Y.; Luo, S.W.; Chen, Q.; Guo, Q. X. Organometallics 2004, 23, 2114. doi: 10.1021/om034067h
34. [34]
  (34) Liu, Y.; Liu, J.W.; Yang, X. Z. Acta Phys. -Chim. Sin. 2002, 18, 1068. [刘跃, 刘佳雯, 杨小震. 物理化学学报, 2002, 18, 1068.] doi: 10.3866/PKU.WHXB20021203
35. [35]
  (35) Li, Z.; Jiang, Y. Y.; Fu, Y. Chem. Eur. J. 2012, 18, 4345. doi: 10.1002/chem.v18.14
36. [36]
  (36) Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680. doi: 10.1021/jo702497p
37. [37]
  (37) Joshi-Pangu, A.; Ganesh, M.; Biscoe, M. R. Org. Lett. 2011, 13, 1218. doi: 10.1021/ol200098d
38. [38]
  (38) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. doi: 10.1021/ja00515a028
39. [39]
  (39) Bakac, A.; Espenson, J. H. J. Am. Chem. Soc. 1986, 108, 719. doi: 10.1021/ja00264a024
40. [40]
  (40) Besora, M.; Carreón-Macedo, J. L.; Cimas, Á.; Harvey, J. N. Adv. Inorg. Chem. 2009, 61, 573. doi: 10.1016/S0898-8838(09)00210-4
41. [41]
  (41) Phapale, V. B.; Guisán-Ceinos, M.; Buñuel, E.; Cárdenas, D. J. Chem. Eur. J. 2009, 15, 12681. doi: 10.1002/chem.v15:46
42. [42]
  (42) Moncomble, A.; Le Floch, P.; smini, C. Chem. Eur. J. 2009, 15, 4770. doi: 10.1002/chem.v15:19
43. [43]
  (43) Li, Z.; Zhang, S. L.; Fu, Y.; Guo, Q. X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 8815. doi: 10.1021/ja810157e
44. [44]
  (44) Czaplik, W. M.; Mayer, M.; Jacobi vonWangelin, A. Angew. Chem. Int. Edit. 2009, 48, 607. doi: 10.1002/anie.v48:3
45. [45]
  (45) Amatore, M.; smini, C. Chem. Commun. 2008, 5019.
46. [46]
  (46) Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592. doi: 10.1021/ja906803t
47. [47]
  (47) Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146. doi: 10.1021/ja301769r
48. [48]
  (48) Jiang, F.; Ren, Q. J. Organomet. Chem. 2014, 757, 72. doi: 10.1016/j.jorganchem.2013.12.047
1. [1]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
2. [2]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
3. [3]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
4. [4]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
5. [5]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
6. [6]
  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
7. [7]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
8. [8]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
9. [9]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
10. [10]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
11. [11]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
12. [12]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
13. [13]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
14. [14]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
15. [15]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
16. [16]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
17. [17]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
18. [18]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
19. [19]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
20. [20]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047

Get Citation

PDF

XML

Metrics

PDF Downloads(717)
Abstract views(762)
HTML views(46)

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