Citation: WEI Yun, ZHOU Shuang-Liu, WANG Shao-Wu. Synthesis, Crystal Structure and Catalytic Activity of a Dinuclear Aluminum Alkyl Complex[J]. Chinese Journal of Structural Chemistry, ;2016, 35(2): 307-312. doi: 10.14102/j.cnki.0254-5861.2011-0823 shu

Synthesis, Crystal Structure and Catalytic Activity of a Dinuclear Aluminum Alkyl Complex

  • Corresponding author: ZHOU Shuang-Liu,  WANG Shao-Wu, 
  • Received Date: 25 May 2015
    Available Online: 23 July 2015

    Fund Project: The project was supported by the National Natural Science Foundation of China (21372010, 21372009) (21372010, 21372009)

  • Treatment of indolyl-3-aldimines (3-tBuN=CH)C8H5NH with AlMe3 afforded the deprotonated indolyl aluminum complex cis-[(μ-η1:η1-3-tBuN=CH)C8H5NAlMe2]2, and its crystal structure was determined by X-ray single-crystal diffraction. The crystal belongs to the orthorhombic system, space group P21212 with a = 14.590(9), b = 15.860(2), c = 13.266(8) Å, μ = 0.118 mm-1, Mr = 512.64, V = 3069.5(3) Å3, Z = 4, Dc = 1.109 g/cm3, F(000) = 1104, R = 0.0451 and wR = 0.0937 for 4978 observed reflections with I > 2σ(I). In addition, the title compound exhibited a high catalytic activity toward the addition of amines to carbodiimide to form guanidines.
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    1. [1]

      (1) (a) Roesky, H. W.; Kumar, S. S. Chemistry of aluminium(I). Chem. Commun. 2005, 4027-4038.

    2. [2]

      (b) Timoshkin, A. Y. Group 13 imido metallanes and their heavier analogs [RMYR']n (M = Al, Ga, In; Y = N, P, As, Sb). Coord. Chem. Rev. 2005, 249, 2094-2031.

    3. [3]

      (2) Tsai, C. F.; Chen, H. J.; Chang, J. C.; Hung, C. H.; Lai, C. C.; Hu, C. H.; Huang, J. H. Metal-induced coordination inversion and carbon-nitrogen bond rearrangement. Structurally characterized phenyl isocyanate inserted into aluminum methyl compounds and O- and N-bound aluminum compounds. Inorg. Chem. 2004, 43, 2183-2188.

    4. [4]

      (3) (a) Normand, M.; Kirillov, E.; Roisnel, T.; Carpentier, J. F. Meerwein-ponndorf-verley-type reduction processes in aluminum and indium isopropoxide complexes of imino-phenolate ligands. Organometallics 2012, 31, 5511-5519.

    5. [5]

      (b) Romain, C.; Fliedel, C.; Bellemin-Laponnaz, S.; Dagorne, S. NHC bis-phenolate aluminum chelates: synthesis, structure, and use in lactide and trimethylene carbonate polymerization. Organometallics 2014, 33, 5730-5739.

    6. [6]

      (4) (a) Wang, Y.; Ma, H. Y. Exploitation of dinuclear salan aluminum complexes for versatile copolymerization of ε-caprolactone and L-lactide. Chem. Comm. 2012, 48, 6729-6731.

    7. [7]

      (b) Wu, J.; Yu, T. L.; Chen, C. T.; Lin, C. C. Recent developments in main group metal complexes catalyzed/initiated polymerization of lactides and related cyclic esters. Coord. Chem. Rev. 2006, 250, 602-626.

    8. [8]

      (5) (a) Hormnirun, P.; Marshall, E. L.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands. J. Am. Chem. Soc. 2004, 126, 2688-2689.

    9. [9]

      (b) Nomura, N.; Ishii, R.; Akakura, M.; Aoi, K. Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: exploration of a chain-end control mechanism. J. Am. Chem. Soc. 2002, 124, 5938-5939.

    10. [10]

      (6) Liu, J. P.; Ma, H. Y. Aluminum complexes with bidentate amido ligands: synthesis, structure and performance on ligand-initiated ring-opening polymerization of rac-lactide. Dalton Trans. 2014, 43, 9098-9110.

    11. [11]

      (7) Yang, Y.; Zhao, N.; Zhu, H. P.; Roesky, H. W. Syntheses and reactions of derivatives of (pyrrolylaldiminato)germanium(II) and -aluminum(III). Organometallics 2012, 31, 1958-1964.

    12. [12]

      (8) Cui, C. M.; Roesky, H. W.; Schmidt, H. G.; Noltemeyer, M.; Hao, H.; Cimpoesu, F. Synthesis and structure of a monomeric aluminum(I) compound [{HC(CMeNAr)2}Al] (Ar = 2,6-iPr2C6H3): a stable aluminum analogue of a carbene. Angew. Chem. Int. Ed. 2000, 39, 4274-4276.

    13. [13]

      (9) (a) Bergman, R. G.; Koller, J. Highly efficient aluminum-catalyzed hydro-amination/-hydrazination of carbodiimides. Organometallics 2010, 29, 5946-5952.

    14. [14]

      (b) Koller, J.; Bergman, R. G. Synthesis, characterization, and reactivity of aluminum alkyl/amide complexes supported by guanidinate and monoanionic OCO-pincer ligands. Organometallics 2010, 29, 3350-3356.

    15. [15]

      (10) (a) Scott, J.; Gambarotto, S.; Korobkov, I.; Knijnenburg, Q.; Bruin, B.; Budzelaar, P. H. M. Formation of a paramagnetic Al complex and extrusion of Fe during the reaction of (diiminepyridine)Fe with AlR3 (R = Me, Et). J. Am. Chem. Soc. 2005, 127, 17204-17206.

    16. [16]

      (b) Myers, T. W.; Kazem, N.; Stoll, S.; Britt, R. D.; Shanmugam, M.; Berben, L. A. A redox series of aluminum complexes: characterization of four oxidation states including a ligand biradical state stabilized via exchange coupling. J. Am. Chem. Soc. 2011, 133, 8662-8672.

    17. [17]

      (11) (a) Li, L.; Liu, B.; Liu, D. T.; Wu, C.; Li, S. H.; Liu, B.; Cui, D. M. Copolymerization of ε-caprolactone and L-lactide catalyzed by multinuclear aluminum complexes: an immortal approach. Organometallics 2014, 33, 6474-6480.

    18. [18]

      (b) Iwasa, N.; Katao, S.; Liu, J.; Fujiki, M.; Furukawa, Y.; Nomura, K. Notable effect of fluoro substituents in the imino group in ring-opening polymerization of ε-caprolactone by Al complexes containing phenoxyimine ligands. Organometallics 2009, 28, 2179-2187.

    19. [19]

      (12) (a) Evans, W. J.; Brady, J. C.; Ziller, J. W. Flexibility in the coordination chemistry of the 2,3-dimethylindolide ligand with potassium, yttrium, and samarium. Inorg. Chem. 2002, 41, 3340-3346;

    20. [20]

      (b) Zhu, G.; Tanski, J. M.; Churchill, D. G.; Janak, K. E.; Parkin, G. The reactivity of Mo(PMe3)6 towards heterocyclic nitrogen compounds: transformations relevant to hydrodenitrogenation. J. Am. Chem. Soc. 2002, 124, 13658-13659.

    21. [21]

      (13) (a) Zhu, X. C.; Zhou, S. L.; Wang, S. W.; Wei, Y.; Zhang, L. J.; Wang, F. H.; Wang, S. Y.; Feng, Z. J. Rare-earth metal complexes having an unusual indolyl-1,2-dianion through C-H activation with a novel η1:(μ2-η1:η1) bonding with metals. Chem. Commun. 2012, 48, 12020-12022.

    22. [22]

      (b) Zhu, X. C.; Wang, S. W.; Zhou, S. L.; Wei, Y.; Zhang, L. J.; Wang, F. H.; Feng, Z. J.; Guo, L. P.; Mu, X. L. Lanthanide amido complexes incorporating amino-coordinate-lithium bridged bis(indolyl) ligands: synthesis, characterization, and catalysis for hydrophosphonylation of aldehydes and aldimines. Inorg. Chem. 2012, 51, 7134-7143.

    23. [23]

      (c) Feng, Z. J.; Zhu, X. C.; Wang, S. Y.; Wang, S. W.; Zhou, S. L.; Wei, Y.; Zhang, G. C.; Deng, B. J.; Mu, X. L. Synthesis, structure, and reactivity of lanthanide complexes incorporating indolyl ligands in novel hapticities. Inorg. Chem. 2013, 52, 9549-9556.

    24. [24]

      (d) Zhang, G. C.; Wei, Y.; Guo, L. P.; Zhu, X. C.; Wang, S. W.; Zhou, S. L.; Mu, X. L. Dinuclear rare-earth metal alkyl complexes supported by indolyl ligands in μ-η2:η1:η1 hapticities and their high catalytic activity for isoprene 1,4-cis-polymerization. Chem. Eur. J. 2015, 21, 2519-2526.

    25. [25]

      (14) Wei, Y.; Wang, S. W.; Zhou, S. L.; Feng, Z. J.; Guo, L. P.; Zhu, X. C.; Mu, X. L.; Yao, F. S. Aluminum alkyl complexes supported by bidentate N, N ligands: synthesis, structure, and catalytic activity for guanylation of amines. Organometallics 2015, 34, 1882-1889.

    26. [26]

      (15) Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structure. University of Göttingen, Germany 1997.

    27. [27]

      (16) Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.

    28. [28]

      (17) Zhang, W. X.; Li, D. Z.; Wang, Z. T.; Xi, Z. F. Alkyl aluminum-catalyzed addition of amines to carbodiimides: a highly efficient route to substituted guanidines. Organometallics 2009, 28, 882-887.

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