铁催化芳基格氏试剂的联芳交叉偶联的反应机理

引用本文: 任清华, 沈晓燕. 铁催化芳基格氏试剂的联芳交叉偶联的反应机理[J]. 物理化学学报, 2015, 31(5): 852-858. doi: 10.3866/PKU.WHXB201503026 shu

Citation: REN Qing-Hua, SHEN Xiao-Yan. Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents[J]. Acta Physico-Chimica Sinica, 2015, 31(5): 852-858. doi: 10.3866/PKU.WHXB201503026 shu

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

任清华 ,
沈晓燕

基金项目:
上海大学高性能计算平台"

自强4000"

与上海市高等教育内涵建设"

工程"

材料基因工程"

项目(B.58-B111-12-101, B.58-B111-12-103)资助 (B.58-B111-12-101, B.58-B111-12-103)

摘要:

利用密度泛函理论(DFT)计算研究了[Fe(MgBr)₂]催化的邻氯苯乙稀与溴代苯基镁反应生成联芳化合物的交叉偶联反应的机理. 研究了两个机理. 机理A包括三个基本步骤: (I) 氧化[Fe(MgBr)₂]生成[Ar-Fe(MgBr)],(II) 加成产生[Ar-(phenyl)-Fe(MgBr)₂], (III) 还原消除回到[Fe(MgBr)₂]. 机理B不形成[Ar-Fe(MgBr)]. 在第一步,溴代苯基镁在[Cl-Mg-Br]离解形成[Ar-Fe(MgBr)]之前直接进攻氧化加成后的中间体. 考虑溶剂效应后, 机理B优于机理A. 无论机理A还是机理B, 整个催化循环过程的决速步骤都是[Ar-(phenyl)-Fe(MgBr)₂]的还原消除再生催化剂[Fe(MgBr)₂]的步骤, 使用导体极化连续模型(CPCM)方法计算其在四氢呋喃溶剂中的吉布斯自由能(ΔG_sol)是82.98 kJ·mol^-1.

关键词:

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

1.
Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, P. R. China
Received Date: 25 December 2014
Available Online: 08 May 2015
Fund Project:
上海大学高性能计算平台"

自强4000"

与上海市高等教育内涵建设"

工程"

材料基因工程"

项目(B.58-B111-12-101, B.58-B111-12-103)资助

Abstract:

Mechanisms for the [Fe(MgBr)₂] catalyzed cross-coupling reaction between ortho-chlorostyrene and phenylmagnesium bromide to form biaryl were studied using density functional theory (DFT) calculations. We investigated two mechanisms. Cycle A included three basic steps: (I) oxidation of [Fe(MgBr)₂] to obtain [Ar- Fe(MgBr)], (II) addition to yield [Ar-(phenyl)-Fe(MgBr)₂], and (III) reductive elimination to return to [Fe(MgBr)₂]. Cycle B did not form [Ar-Fe(MgBr)]. In the first step, phenylmagnesium bromide attacks the intermediate of the oxidative addition directly before [Cl-Mg-Br] dissociates to form [Ar-Fe(MgBr)]. The catalytic Cycle B is favored over the catalytic Cycle Awhen considering the solvent effect. The rate-limiting step in the overall catalytic cycle for both Cycle A and Cycle B is the reductive elimination of [Ar-(phenyl)-Fe(MgBr)₂] to regenerate the catalyst [Fe(MgBr)₂], where the Gibbs free energy in solvent tetrahydrofuran (THF), ΔG_sol, is 82.98 kJ ·mol^-1, as determined using the conductor polarized continuum model (CPCM) method.

Key words:

1. [1]
  
  (1) Negishi, E. Accounts Chem. Res. 1982, 15, 340. doi: 10.1021/ar00083a001
  (1) Negishi, E. Accounts Chem. Res. 1982, 15, 340. doi: 10.1021/ar00083a001
2. [2]
  (2) Yang, Y.; Oldenhuis, N. J.; Buchwald, S. L. Angew. Chem. Int. Edit. 2013, 125, 643. doi: 10.1002/ange.201207750(2) Yang, Y.; Oldenhuis, N. J.; Buchwald, S. L. Angew. Chem. Int. Edit. 2013, 125, 643. doi: 10.1002/ange.201207750
3. [3]
  (3) Blangetti, M.; Rosso, H.; Prandi, C.; Dea stino, A.; Venturello, P. Molecules 2013, 18, 1188. doi: 10.3390/molecules18011188(3) Blangetti, M.; Rosso, H.; Prandi, C.; Dea stino, A.; Venturello, P. Molecules 2013, 18, 1188. doi: 10.3390/molecules18011188
4. [4]
  (4) Miyaura, N.; Suzuki, A. J. Chem. Soc. Chem. Commun. 1979, 19, 866. doi: 10.1039/C39790000866(4) Miyaura, N.; Suzuki, A. J. Chem. Soc. Chem. Commun. 1979, 19, 866. doi: 10.1039/C39790000866
5. [5]
  (5) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320. doi: 10.1021/jo00979a024(5) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320. doi: 10.1021/jo00979a024
6. [6]
  (6) Cabri, W.; Candiani, I. Accounts Chem. Res. 1995, 28, 2. doi: 10.1021/ar00049a001(6) Cabri, W.; Candiani, I. Accounts Chem. Res. 1995, 28, 2. doi: 10.1021/ar00049a001
7. [7]
  (7) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636. doi: 10.1021/ja00479a077(7) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636. doi: 10.1021/ja00479a077
8. [8]
  (8) Yabe, Y.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Tetrahedron 2010, 66, 8654. doi: 10.1016/j.tet.2010.09.027(8) Yabe, Y.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Tetrahedron 2010, 66, 8654. doi: 10.1016/j.tet.2010.09.027
9. [9]
  (9) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374. doi: 10.1021/ja00767a075(9) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374. doi: 10.1021/ja00767a075
10. [10]
  (10) Yang, L. M.; Huang, L. F.; Luh, T. Y. Org. Lett. 2004, 6, 1461. doi: 10.1021/ol049686g(10) Yang, L. M.; Huang, L. F.; Luh, T. Y. Org. Lett. 2004, 6, 1461. doi: 10.1021/ol049686g
11. [11]
  (11) Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756. doi: 10.1021/ja9027378(11) Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756. doi: 10.1021/ja9027378
12. [12]
  (12) Torssell, K. B. Natural Product Chemistry: a Mechanistic and Biosynthetic Approach to Secondary Metabolism; JohnWiley & Sons: New Jersey, 1983; p 401.(12) Torssell, K. B. Natural Product Chemistry: a Mechanistic and Biosynthetic Approach to Secondary Metabolism; JohnWiley & Sons: New Jersey, 1983; p 401.
13. [13]
  (13) Hassan, J.; Sevignon, M.; zzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. doi: 10.1021/cr000664r(13) Hassan, J.; Sevignon, M.; zzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. doi: 10.1021/cr000664r
14. [14]
  (14) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007(14) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
15. [15]
  (15) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem. Int. Edit. 2005, 44, 5384.(15) Bringmann, G.; Mortimer, A. J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem. Int. Edit. 2005, 44, 5384.
16. [16]
  (16) Kirsch, P.; Bremer, M. Angew. Chem. Int. Edit. 2000, 39, 4216.(16) Kirsch, P.; Bremer, M. Angew. Chem. Int. Edit. 2000, 39, 4216.
17. [17]
  (17) Bauer, E. B. Curr. Org. Chem. 2008, 12, 1341. doi: 10.2174/ 138527208786241556(17) Bauer, E. B. Curr. Org. Chem. 2008, 12, 1341. doi: 10.2174/ 138527208786241556
18. [18]
  (18) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217. doi: 10.1021/cr040664h(18) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217. doi: 10.1021/cr040664h
19. [19]
  (19) Czaplik, W. M.; Mayer, M.; Cvengros, J.; vonWangelin, A. J. ChemSusChem 2009, 2, 396. doi: 10.1002/cssc.v2:5(19) Czaplik, W. M.; Mayer, M.; Cvengros, J.; vonWangelin, A. J. ChemSusChem 2009, 2, 396. doi: 10.1002/cssc.v2:5
20. [20]
  (20) Sherry, B. D.; Furstner, A. Accounts Chem. Res. 2008, 41, 1500. doi: 10.1021/ar800039x(20) Sherry, B. D.; Furstner, A. Accounts Chem. Res. 2008, 41, 1500. doi: 10.1021/ar800039x
21. [21]
  (21) Furstner, A.; Leitner, A. Angew. Chem. Int. Edit. 2002, 41, 609.(21) Furstner, A.; Leitner, A. Angew. Chem. Int. Edit. 2002, 41, 609.
22. [22]
  (22) Furstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. doi: 10.1021/ja027190t(22) Furstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856. doi: 10.1021/ja027190t
23. [23]
  (23) Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108. doi: 10.1039/b801794h(23) Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108. doi: 10.1039/b801794h
24. [24]
  (24) Furstner, A.; Martin, R. Chem. Lett. 2005, 34, 624. doi: 10.1246/cl.2005.624(24) Furstner, A.; Martin, R. Chem. Lett. 2005, 34, 624. doi: 10.1246/cl.2005.624
25. [25]
  (25) Furstner, A.; Martin, R.; Krause, H.; Seidel, G.; ddard, R.; Lehmann, C.W. J. Am. Chem. Soc. 2008, 130, 8773. doi: 10.1021/ja801466t(25) Furstner, A.; Martin, R.; Krause, H.; Seidel, G.; ddard, R.; Lehmann, C.W. J. Am. Chem. Soc. 2008, 130, 8773. doi: 10.1021/ja801466t
26. [26]
  (26) Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078. doi: 10.1021/ja901262g(26) Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078. doi: 10.1021/ja901262g
27. [27]
  (27) Scheiper, B.; Bonnekessel, M.; Krause, H.; Furstner, A. J. Org. Chem. 2004, 69, 3943. doi: 10.1021/jo0498866(27) Scheiper, B.; Bonnekessel, M.; Krause, H.; Furstner, A. J. Org. Chem. 2004, 69, 3943. doi: 10.1021/jo0498866
28. [28]
  (28) Molander, G. A.; Rahn, B. J.; Shubert, D. C. Tetrahedron Lett. 1983, 24, 5449. doi: 10.1016/S0040-4039(00)94109-1(28) Molander, G. A.; Rahn, B. J.; Shubert, D. C. Tetrahedron Lett. 1983, 24, 5449. doi: 10.1016/S0040-4039(00)94109-1
29. [29]
  (29) Quintin, J.; Franck, X.; Hocquemiller, R.; Figadere, B. Tetrahedron Lett. 2002, 43, 3547. doi: 10.1016/S0040-4039(02)00568-3(29) Quintin, J.; Franck, X.; Hocquemiller, R.; Figadere, B. Tetrahedron Lett. 2002, 43, 3547. doi: 10.1016/S0040-4039(02)00568-3
30. [30]
  (30) Hocek, M.; Dvorakova, H. J. Org. Chem. 2003, 68, 5773. doi: 10.1021/jo034351i(30) Hocek, M.; Dvorakova, H. J. Org. Chem. 2003, 68, 5773. doi: 10.1021/jo034351i
31. [31]
  (31) Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844. doi: 10.1021/ja073084l(31) Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844. doi: 10.1021/ja073084l
32. [32]
  (32) Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949. doi: 10.1021/ja9039289(32) Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949. doi: 10.1021/ja9039289
33. [33]
  (33) Mayer, M.; Welther, A.; vonWangelin, A. J. ChemCatChem 2011, 3, 1567. doi: 10.1002/cctc.v3.10(33) Mayer, M.; Welther, A.; vonWangelin, A. J. ChemCatChem 2011, 3, 1567. doi: 10.1002/cctc.v3.10
34. [34]
  (34) Clayton, H. S.; Moss, J. R.; Dry, M. E. J. Organomet. Chem. 2003, 688, 181. doi: 10.1016/j.jorganchem.2003.08.044(34) Clayton, H. S.; Moss, J. R.; Dry, M. E. J. Organomet. Chem. 2003, 688, 181. doi: 10.1016/j.jorganchem.2003.08.044
35. [35]
  (35) Knolker, H. J. Chem. Soc. Rev. 1999, 28, 151. doi: 10.1039/a705401g(35) Knolker, H. J. Chem. Soc. Rev. 1999, 28, 151. doi: 10.1039/a705401g
36. [36]
  (36) Gulak, S.; vonWangelin, A. J. Angew. Chem. Int. Edit. 2012, 51, 1357. doi: 10.1002/anie.201106110(36) Gulak, S.; vonWangelin, A. J. Angew. Chem. Int. Edit. 2012, 51, 1357. doi: 10.1002/anie.201106110
37. [37]
  (37) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502. doi: 10.1021/jo00865a019(37) Smith, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502. doi: 10.1021/jo00865a019
38. [38]
  (38) Bogdanovic, B.; Schwickardi, M. Angew. Chem. Int. Edit. 2000, 39, 4610.(38) Bogdanovic, B.; Schwickardi, M. Angew. Chem. Int. Edit. 2000, 39, 4610.
39. [39]
  (39) Kleimark, J.; Hedstrom A.; Larsson P. F.; Johansson, C.; Norrby, P. ChemCatChem 2009, 1, 152. doi: 10.1002/cctc.v1:1(39) Kleimark, J.; Hedstrom A.; Larsson P. F.; Johansson, C.; Norrby, P. ChemCatChem 2009, 1, 152. doi: 10.1002/cctc.v1:1
40. [40]
  (40) Ren, Q.; Guan, S.; Jiang, F.; Fang, J. J. Phys. Chem. A 2013, 117, 756. doi: 10.1021/jp3045498(40) Ren, Q.; Guan, S.; Jiang, F.; Fang, J. J. Phys. Chem. A 2013, 117, 756. doi: 10.1021/jp3045498
41. [41]
  (41) Czaplik, W. M.; Mayer, M.; vonWangelin, A. J. ChemCatChem 2011, 3, 135. doi: 10.1002/cctc.201000276(41) Czaplik, W. M.; Mayer, M.; vonWangelin, A. J. ChemCatChem 2011, 3, 135. doi: 10.1002/cctc.201000276
42. [42]
  (42) Mo, Z.; Zhang, Q.; Deng, L. Organometallics 2012, 31, 6518. doi: 10.1021/om300722g(42) Mo, Z.; Zhang, Q.; Deng, L. Organometallics 2012, 31, 6518. doi: 10.1021/om300722g
43. [43]
  (43) Becke, A. D. Phys. Rev. A 1988, 38, 3098. doi: 10.1103/PhysRevA.38.3098(43) Becke, A. D. Phys. Rev. A 1988, 38, 3098. doi: 10.1103/PhysRevA.38.3098
44. [44]
  (44) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913(44) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
45. [45]
  (45) Hertwig, R. H.; Koch, W. Chem. Phys. Lett. 1997, 268, 345. doi: 10.1016/S0009-2614(97)00207-8(45) Hertwig, R. H.; Koch, W. Chem. Phys. Lett. 1997, 268, 345. doi: 10.1016/S0009-2614(97)00207-8
46. [46]
  (46) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785(46) Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
47. [47]
  (47) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623. doi: 10.1021/j100096a001(47) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623. doi: 10.1021/j100096a001
48. [48]
  (48) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200. doi: 10.1139/p80-159(48) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200. doi: 10.1139/p80-159
49. [49]
  (49) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision C.02; Gaussian Inc.; Wallingford, CT, 2004.(49) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision C.02; Gaussian Inc.; Wallingford, CT, 2004.
50. [50]
  (50) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. doi: 10.1063/1.438955(50) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. doi: 10.1063/1.438955
51. [51]
  (51) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. doi: 10.1063/1.438980(51) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. doi: 10.1063/1.438980
52. [52]
  (52) Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta. 1990, 77, 123. doi: 10.1007/BF01114537(52) Andrae, D.; Haussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta. 1990, 77, 123. doi: 10.1007/BF01114537
53. [53]
  (53) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669. doi: 10.1002/jcc.10189(53) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669. doi: 10.1002/jcc.10189
54. [54]
  (54) Castejon, H.; Wiberg, K. B. J. Am. Chem. Soc. 1999, 121, 2139. doi: 10.1021/ja983736t(54) Castejon, H.; Wiberg, K. B. J. Am. Chem. Soc. 1999, 121, 2139. doi: 10.1021/ja983736t
55. [55]
  (55) Perng, B. C.; Newton, M. D.; Raineri, F. O.; Friedman, H. L. J. Chem. Phys. 1996, 104, 7153 and 7177.(55) Perng, B. C.; Newton, M. D.; Raineri, F. O.; Friedman, H. L. J. Chem. Phys. 1996, 104, 7153 and 7177.
56. [56]
  (56) Najafi, M.; Zahedi, M.; Klein, E. Comput. Theor. Chem. 2011, 978, 16. doi: 10.1016/j.comptc.2011.09.014(56) Najafi, M.; Zahedi, M.; Klein, E. Comput. Theor. Chem. 2011, 978, 16. doi: 10.1016/j.comptc.2011.09.014
57. [57]
  (57) Schubert, G.; Papai, I. J. Am. Chem. Soc. 2003, 125, 14847. doi: 10.1021/ja035791u(57) Schubert, G.; Papai, I. J. Am. Chem. Soc. 2003, 125, 14847. doi: 10.1021/ja035791u
58. [58]
  (58) Belelli, P. G.; Damiani, D. E.; Castellani, N. J. Chem. Phys. Lett. 2005, 401, 515. doi: 10.1016/j.cplett.2004.11.089(58) Belelli, P. G.; Damiani, D. E.; Castellani, N. J. Chem. Phys. Lett. 2005, 401, 515. doi: 10.1016/j.cplett.2004.11.089
59. [59]
  (59) Feng, J.; Ren, Q. H. Acta. Phys. -Chim. Sin. 2014, 30, 821. [蒋峰, 任清华. 物理化学学报, 2014, 30, 821.](59) Feng, J.; Ren, Q. H. Acta. Phys. -Chim. Sin. 2014, 30, 821. [蒋峰, 任清华. 物理化学学报, 2014, 30, 821.]
60. [60]
  (60) Nova, A.; Ujaque, G.; Maseras, F.; Liedos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571. doi: 10.1021/ja0635736
  (60) Nova, A.; Ujaque, G.; Maseras, F.; Liedos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571. doi: 10.1021/ja0635736

扫一扫看文章

计量

PDF下载量: 315
文章访问数: 1106
HTML全文浏览量: 121

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

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

铁催化芳基格氏试剂的联芳交叉偶联的反应机理

English

Reaction Mechanism for the Iron-Catalyzed Biaryl Cross-Coupling of Aryl Grignard Reagents

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs