Citation: Liu Jian, Xiao Jie, Mondal Sudipta, Leng Xuebing, Deng Liang. Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3380-3389. doi: 10.6023/cjoc202005089 shu

Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Deng Liang, deng@sioc.ac.cn
Received Date: 29 May 2020
Revised Date: 27 June 2020
Available Online: 30 June 2020
Fund Project: the National Key Research and Development Program of the Ministry of Science and Technology 2016YFA0202900AS Strategic Pilot Science And Technology Special XDB20000000the Natural Science Foundation of China 21690062Project supported by the National Key Research and Development Program of the Ministry of Science and Technology (No. 2016YFA0202900), the Natural Science Foundation of China (Nos. 21725104, 21690062, 21821002), CAS Strategic Pilot Science And Technology Special (No. XDB20000000), and the Program of Shanghai Academic Research Leader (No. 19XD1424800)the Natural Science Foundation of China 21725104the Natural Science Foundation of China 21821002the Program of Shanghai Academic Research Leader 19XD1424800

Figures(15)

Treatment of Bu^tPCl₂ with 2 equiv. of (2, 4, 6-Me₃C₆H₂)(2-LiC₆H₄)NLi and (2, 6-Cl₂C₆H₃)(2-LiC₆H₄)NLi, which were generated in situ by the interaction of (2, 4, 6-Me₃C₆H₂)(2-BrC₆H₄)NH and (2, 6-Cl₂C₆H₃)(2-BrC₆H₄)NH with 2 equiv. of BuⁿLi, followed by quenching with water, afforded new tridentate diamine-phosphine compounds (o-(N-(2, 4, 6-Me₃C₆H₂)-NH)C₆H₄)₂PBu^t and (o-(N-(2, 6-Cl₂C₆H₃)NH)C₆H₄)₂PBu^t (denoted as H₂(^MesN₂P^Bu-t) and H₂(^dcpN₂P^Bu-t)), respectively. H₂(^MesN₂P^Bu-t) and H₂(^dcpN₂P^Bu-t) underwent amine-elimination reaction with[Fe(N(SiMe₃)₂)₂]₂ (0.5 equiv.) to afford iron(Ⅱ) complexes[(κ³-N, N, P-^MesN₂P^Bu-t)Fe(OEt₂)] (1) and[(κ³-N, N, P-^dcpN₂P^Bu-t)Fe(OEt₂)] (2) bearing tridentate diamido-phosphine ligands. Treatment of 1 with organic diazo compounds (p-tolyl)₂CN₂ and PhC(N₂)CO₂Et rendered the formation of diazo coordinated iron complexes[(κ³-N, N, P-^MesN₂P^Bu-t)Fe(η²-N, N-(p-tolyl)₂CN₂)] (3) and[(κ³-N, N, P-^MesN₂P^Bu-t)Fe(κ²-N, O-PhC(N₂)-CO₂Et)] (4), respectively. Complex 2 can catalyze the conversion of (p-tolyl)₂CN₂ to (p-tolyl)₂C=NN=C(tolyl-p)₂. Treatment of 2 with organic diazo compound DmpC(N₂)H rendered the formation of a high-spin iron(Ⅱ) complex featuring the tridentate bisamido-phosphine ylide ligand[(κ³-N, N, C-^dcpN₂P^Bu-tC^{H, Dmp})Fe] (5). These complexes have been characterized by elemental analysis, ¹H NMR, solution magnetic susceptibility measurements, zero-field ⁵⁷Fe Mössbauer spectroscopy and single-crystal X-ray diffraction studies. The spectroscopic data in combination with theoretical study suggest that complex 3 can be viewed as a low-spin iron(IV) imido complex featuring an dianionic ligand[η²-N, N-(p-tolyl)₂CN₂]^2-, whereas 4 has an intermediate-spin iron(Ⅲ) center that is antiferromagnetically coupled to a diazoalkane radical anion[κ²-N, O-PhC(N₂)-CO₂Et)]^•1-.
- iron,
- diazo compounds,
- diamido-phosphine ligand
1. [1]
  Herrmann, W. A. Angew. Chem., Int. Ed. 1978, 17, 800. doi: 10.1002/anie.197808001
2. [2]
  Sutton, D. Chem. Rev. 1993, 93, 995. doi: 10.1021/cr00019a008
3. [3]
  Mizobe, Y.; Ishii, Y.; Hidai, M. Coord. Chem. Rev. 1995, 139, 281. doi: 10.1016/0010-8545(94)01118-U
4. [4]
  Poverenov, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organo- metallics 2005, 24, 5937.
5. [5]
  Samant, R. G.; Graham, T. W.; Rowsell, B. D.; McDonald, R.; Cowie, M. Organometallics 2008, 27, 3070. doi: 10.1021/om700756q
6. [6]
  Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411. doi: 10.1021/cr00078a008
7. [7]
  Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3740. doi: 10.1002/anie.200601234
8. [8]
  Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748. doi: 10.1002/anie.200600085
9. [9]
  Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760. doi: 10.1002/anie.200600680
10. [10]
  Zhu, S.-F.; Zhou, Q.-L. Natl. Sci. Rev. 2014, 1, 580. doi: 10.1093/nsr/nwu019
11. [11]
  Albertin, G.; Antoniutti, S.; Forcolin, M.; Gasparato, D. Polyhedron 2016, 104, 46. doi: 10.1016/j.poly.2015.11.021
12. [12]
  Albertin, G.; Antoniutti, S.; Botter, A.; Castro, J. Inorg. Chem. 2015, 54, 2091. doi: 10.1021/ic502963n
13. [13]
  Albertin, G.; Antoniutti, S.; Castro, J.; Dottorello, G. Dalton Trans 2015, 44, 9289. doi: 10.1039/C5DT00755K
14. [14]
  Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Castro, J.; Marzaro, L. Dalton Trans 2015, 44, 15470. doi: 10.1039/C5DT02113H
15. [15]
  Werner, H.; Mahr, N.; Wolf, J.; Fries, A.; Laubender, M.; Bleuel, E.; Garde, R.; Lahuerta, P. Organometallics 2003, 22, 3566. doi: 10.1021/om0302037
16. [16]
  Bonyhady, S. J.; Goldberg, J. M.; Wedgwood, N.; Dugan, T. R.; Eklund, A. G.; Brennessel, W. W.; Holland, P. L. Inorg. Chem. 2015, 54, 5148. doi: 10.1021/acs.inorgchem.5b00673
17. [17]
  Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M.; You, X.-Z. J. Am. Chem. Soc. 2002, 124, 13185. doi: 10.1021/ja020391c
18. [18]
  Bart, S. C.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2007, 129, 7212. doi: 10.1021/ja070056u
19. [19]
  Sazama, G. T.; Betley, T. A. Inorg. Chem. 2014, 53, 269. doi: 10.1021/ic402210j
20. [20]
  Bonyhady, S. J.; DeRosha, D. E.; Vela, J.; Vinyard, D. J.; Cowley, R. E.; Mercado, B. Q.; Brennessel, W. W.; Holland, P. L. Inorg. Chem. 2018, 57, 5959. doi: 10.1021/acs.inorgchem.8b00468
21. [21]
  Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Botter, A.; Castro, J.; Sibilla, F. RSC Adv. 2016, 6, 97650. doi: 10.1039/C6RA22051G
22. [22]
  Russell, S. K.; Hoyt, J. M.; Bart, S. C.; Milsmann, C.; Stieber, S. C. E.; Semproni, S. P.; DeBeer, S.; Chirik, P. J. Chem. Sci. 2014, 5, 1168. doi: 10.1039/C3SC52450G
23. [23]
  Liu, J.; Hu, L.; Wang, L.; Chen, H.; Deng, L. J. Am. Chem. Soc. 2017, 139, 3876. doi: 10.1021/jacs.7b00484
24. [24]
  Xiao, J.; Deng, L. Dalton Trans. 2013, 42, 5607. doi: 10.1039/c3dt50518a
25. [25]
  Smit, T. M.; Tomov, A. K.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2004, 43, 6511. doi: 10.1021/ic0490775
26. [26]
  Cheng, J.; Liu, J.; Leng, X.; Lohmiller, T.; Schnegg, A.; Bill, E.; Ye, S.; Deng, L. Inorg. Chem. 2019, 58, 7634. doi: 10.1021/acs.inorgchem.9b01147
27. [27]
  Chisholm, M. H.; Folting, K.; Huffman, J. C.; Ratermann, A. L. Inorg. Chem. 1984, 23, 2303. doi: 10.1021/ic00183a019
28. [28]
  Sydora, O. L.; Kuiper, D. S.; Wolczanski, P. T.; Lobkovsky, E. B.; Dinescu, A.; Cundari, T. R. Inorg. Chem. 2006, 45, 2008. doi: 10.1021/ic051481w
29. [29]
  Straub, B. F.; Rominger, F.; Hofmann, P. Organometallics 2000, 19, 4305. doi: 10.1021/om000430y
30. [30]
  Olmstead, M. M.; Power, P. P.; Shoner, S. C. Inorg. Chem. 1991, 30, 2547. doi: 10.1021/ic00011a017
31. [31]
  Javed, M. I.; Brewer, M. Org. Lett. 2007, 9, 1789. doi: 10.1021/ol070515w
32. [32]
  Iluc, V. M.; Laskowski, C. A.; Hillhouse, G. L. Organometallics 2009, 28, 6135. doi: 10.1021/om900566k
33. [33]
  Evans, D. F. J. Chem. Soc. 1959, 2003.
34. [34]
  Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data, University of G ttingen, G ttingen, Germany, 1996.
35. [35]
  Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864. doi: 10.1103/PhysRev.136.B864
36. [36]
  Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133. doi: 10.1103/PhysRev.140.A1133
37. [37]
  Neese F.. ORCA-an ab initio, Density Functional and Semiempirical Program Package, Version 4.1.0[J]. Max-Planck Institute for Bioinorganic Chemistry, Mulheim an der Ruhr, Germany, 2017.
38. [38]
  Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
39. [39]
  Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
40. [40]
  Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571. doi: 10.1063/1.463096
41. [41]
  Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829. doi: 10.1063/1.467146
42. [42]
  Pantazis, D. A.; Chen, X.-Y.; Landis, C. R.; Neese, F. J. Chem. Theory Comput. 2008, 4, 908. doi: 10.1021/ct800047t
43. [43]
  Neese, F.; Wennmohs, F.; Hansen, A.; Becker, U. Chem. Phys. 2009, 356, 98. doi: 10.1016/j.chemphys.2008.10.036
44. [44]
  Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456. doi: 10.1002/jcc.21759
45. [45]
  Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104. doi: 10.1063/1.3382344
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