SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3380 - 3389

DOI: https://doi.org/10.6023/cjoc202005089

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

  • Liu Jian ,
  • Xiao Jie ,
  • Mondal Sudipta ,
  • Leng Xuebing ,
  • Deng Liang
Expand
  • State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2020-05-29

  Revised date: 2020-06-27

  Online published: 2020-07-01

Supported by

Project 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).

Fold

Abstract

Treatment of ButPCl2 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)2PBut and (o-(N-(2,6-Cl2C6H3)NH)C6H4)2PBut (denoted as H2(MesN2PBu-t) and H2(dcpN2PBu-t)), respectively. H2(MesN2PBu-t) and H2(dcpN2PBu-t) underwent amine-elimination reaction with[Fe(N(SiMe3)2)2]2 (0.5 equiv.) to afford iron(Ⅱ) complexes[(κ3-N,N,P-MesN2PBu-t)Fe(OEt2)] (1) and[(κ3-N,N,P-dcpN2PBu-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-MesN2PBu-t)Fe(η2-N,N-(p-tolyl)2CN2)] (3) and[(κ3-N,N,P-MesN2PBu-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-dcpN2PBu-tCH,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-.

Key words： iron; diazo compounds; diamido-phosphine ligand

Cite this article

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

References

[1] Herrmann, W. A. Angew. Chem., Int. Ed. 1978, 17, 800.
[2] Sutton, D. Chem. Rev. 1993, 93, 995.
[3] Mizobe, Y.; Ishii, Y.; Hidai, M. Coord. Chem. Rev. 1995, 139, 281.
[4] Poverenov, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organo- metallics 2005, 24, 5937.
[5] Samant, R. G.; Graham, T. W.; Rowsell, B. D.; McDonald, R.; Cowie, M. Organometallics 2008, 27, 3070.
[6] Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411.
[7] Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3740.
[8] Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748.
[9] Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760.
[10] Zhu, S.-F.; Zhou, Q.-L. Natl. Sci. Rev. 2014, 1, 580.
[11] Albertin, G.; Antoniutti, S.; Forcolin, M.; Gasparato, D. Polyhedron 2016, 104, 46.
[12] Albertin, G.; Antoniutti, S.; Botter, A.; Castro, J. Inorg. Chem. 2015, 54, 2091.
[13] Albertin, G.; Antoniutti, S.; Castro, J.; Dottorello, G. Dalton Trans 2015, 44, 9289.
[14] Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Castro, J.; Marzaro, L. Dalton Trans 2015, 44, 15470.
[15] Werner, H.; Mahr, N.; Wolf, J.; Fries, A.; Laubender, M.; Bleuel, E.; Garde, R.; Lahuerta, P. Organometallics 2003, 22, 3566.
[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.
[17] Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M.; You, X.-Z. J. Am. Chem. Soc. 2002, 124, 13185.
[18] Bart, S. C.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2007, 129, 7212.
[19] Sazama, G. T.; Betley, T. A. Inorg. Chem. 2014, 53, 269.
[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.
[21] Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Botter, A.; Castro, J.; Sibilla, F. RSC Adv. 2016, 6, 97650.
[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.
[23] Liu, J.; Hu, L.; Wang, L.; Chen, H.; Deng, L. J. Am. Chem. Soc. 2017, 139, 3876.
[24] Xiao, J.; Deng, L. Dalton Trans. 2013, 42, 5607.
[25] Smit, T. M.; Tomov, A. K.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2004, 43, 6511.
[26] Cheng, J.; Liu, J.; Leng, X.; Lohmiller, T.; Schnegg, A.; Bill, E.; Ye, S.; Deng, L. Inorg. Chem. 2019, 58, 7634.
[27] Chisholm, M. H.; Folting, K.; Huffman, J. C.; Ratermann, A. L. Inorg. Chem. 1984, 23, 2303.
[28] Sydora, O. L.; Kuiper, D. S.; Wolczanski, P. T.; Lobkovsky, E. B.; Dinescu, A.; Cundari, T. R. Inorg. Chem. 2006, 45, 2008.
[29] Straub, B. F.; Rominger, F.; Hofmann, P. Organometallics 2000, 19, 4305.
[30] Olmstead, M. M.; Power, P. P.; Shoner, S. C. Inorg. Chem. 1991, 30, 2547.
[31] Javed, M. I.; Brewer, M. Org. Lett. 2007, 9, 1789.
[32] Iluc, V. M.; Laskowski, C. A.; Hillhouse, G. L. Organometallics 2009, 28, 6135.
[33] Evans, D. F. J. Chem. Soc. 1959, 2003.
[34] Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Göttingen, Germany, 1996.
[35] Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
[36] Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
[37] Neese, F. ORCA-an ab initio, Density Functional and Semiempirical Program Package, Version 4.1.0, Max-Planck Institute for Bioinorganic Chemistry, Mulheim an der Ruhr, Germany, 2017.
[38] Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
[39] Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
[40] Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
[41] Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
[42] Pantazis, D. A.; Chen, X.-Y.; Landis, C. R.; Neese, F. J. Chem. Theory Comput. 2008, 4, 908.
[43] Neese, F.; Wennmohs, F.; Hansen, A.; Becker, U. Chem. Phys. 2009, 356, 98.
[44] Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456.
[45] Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.
Options
Outlines

/

〈 〉