Reductive assembly of cyclobutadienyl and diphosphacyclobutadienyl rings at uranium

Nature Communications

Volumn 4, Issue , 2013, Pages

  Patel, Dipti ^a   McMaster, Jonathan ^a   Lewis, William ^a   Blake, Alexander J ^a   Liddle, Stephen T ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

( 2,2 DIMETHYLPROPYLIDYNE)PHOSPHINE; ACETYLENE DERIVATIVE; CYCLOBUTADIENYL; CYCLOBUTANE DERIVATIVE; CYCLOOCTANE DERIVATIVE; CYCLOOCTATETRAENIDE; DIPHENYLACETYLENE; DIPHOSPHACYCLOBUTADIENYL; LIGAND; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG; URANIUM; URANIUM DERIVATIVE;

ABUNDANCE; COMPUTER SIMULATION; LIGAND; URANIUM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; COMPUTATIONAL FLUID DYNAMICS; CONTROLLED STUDY; CYCLOADDITION; MOLECULAR MODEL; REDUCTION; RING OPENING; STATIC ELECTRICITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 84883148854     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms3323     Document Type: Article

References (60)

1. Kealy, T. J. & Pauson, P. L. A new type of organo-iron compound. Nature 168, 1039-1040 (1951).
2. Miller, S. A., Tebboth, J. A. & Tremaine, J. F. Dicyclopentadienyliron. J. Chem. Soc. 632-635 (1952).
3. Werner, H. At least 60 years of ferrocene: the discovery and rediscovery of the sandwich complexes. Angew. Chem. Int. Ed. 51, 6052-6058 (2012).
4. Elschenbroich, C. Organometallics. 3rd edn (Wiley-VCH,Weinheim, Germany, 2005).
5. Seyferth, D. (Cyclobutadiene)iron tricarbonyl-a case of theory before experiment. Organometallics 22, 2-20 (2003).
6. Astruc, D. Modern arene chemistry (Wiley VCH, Weinheim, Germany, 2002).
7. Efraty, A. Cyclobutadienemetal complexes. Chem. Rev. 77, 691-744 (1977).
8. Donaldson, W. A. Comprehensive Organometallic Chemistry II. (eds Abel, E. W., Stone, F. G. A. & Wilkinson, G.) (Pergamon, Oxford, UK, 1995; 12 Chapter 6.2, pp 623).
9. Arndt, S. & Okuda, J. Mono(cyclopentadienyl) complexes of the rare-earth metals. Chem. Rev. 102, 1953-1976 (2002). (Pubitemid 35377638)
10. Evans, W. J. & Davis, B. L. Chemistry of tris(pentamethylcyclopentadienyl) f-element complexes, (C5Me5)3M. Chem. Rev. 102, 2119-2025 (2002).
11. Bochkarev, M. N. Synthesis, arrangement, and reactivity of arene-lanthanide compounds. Chem. Rev. 102, 2089-2118 (2002).
12. Ephritikhine, M. The vitality of uranium molecular chemistry at the dawn of the XXIst century. Dalton Trans. 2501-2516 (2006). (Pubitemid 43814958)
13. Fox, A. R., Bart, S. C., Meyer, K. & Cummins, C. C. Towards uranium catalysts. Nature 455, 341-349 (2008).
14. Hayton, T. W. Metal-ligand multiple bonding in uranium: structure and reactivity. Dalton Trans. 39, 1145-1158 (2010).
15. King, D. M. et al. Synthesis and structure of a terminal uranium nitride complex. Science 337, 717-720 (2012).
16. La Pierre, H. S. & Meyer, K. Uranium-ligand multiple bonding in uranyl analogues, [LUL]n\+, and the inverse trans influence. Inorg. Chem. 52, 529-539 (2013).
17. Hayton, T. W. Recent developments in actinide-ligand multiple bonding. Chem. Commun. 49, 2956-2973 (2013).
18. Reynolds, L. T. & Wilkinson, G. p-cyclopentadienyl compounds of uranium-IV and thorium-IV. J. Inorg. Nucl. Chem. 2, 246-253 (1956).
19. Wong, C.-H., Yen, T.-M. & Lee, T.-Y. The crystal structure of uranium chloride p-tricyclopentadienyl. Acta Cryst. 18, 340-345 (1965).
20. Streitwieser, Jnr A. & Mu?ller-Westerhoff, U. Bis(cyclooctatetraenyl) uranium (uranocene). A new class of sandwich complexes that utilize atomic f orbitals. J. Am. Chem. Soc. 90, 7364-7364 (1968).
21. Zalkin, A. & Raymond, K. N. The structure of di-p- cyclooctatetraeneuranium (uranocene). J. Am. Chem. Soc. 91, 5667-5668 (1969).
22. Arliguie, T., Lance, M., Nierlich, M., Vigner, J. & Ephritikhine, E. Inverse cycloheptatrienyl sandwich complexes. Crystal structure of [U(BH4)2(OC4H8)5][(BH4)3U(m-Z7:Z7-C7H7)U(BH4)3]. J. Chem. Soc. Chem. Commun. 847-848 (1994).
23. Arliguie, T., Lance, M., Nierlich, M., Vigner, J. & Ephritikhine, E. Synthesis and crystal structure of [K(C12H24O6)][U(C7H7)2], the first cycloheptatrienyl sandwich compound. J. Chem. Soc. Chem. Commun. 183-184 (1995).
24. Cesari, M., Pedretti, U., Zazetta, A., Lugli, G. & Marconi, W. Synthesis and structure of a p-Arene complex of uranium(III)-aluminium chloride. Inorg. Chim. Acta 5, 439-444 (1971).
25. Diaconescu, P. L., Arnold, P. L., Baker, T. A., Mindiola, D. J. & Cummins, C. C. Arene-bridged diuranium complexes: inverted sandwiches supported by d backbonding. J. Am. Chem. Soc. 122, 6108-6109 (2000). (Pubitemid 30451116)
26. Diaconescu, P. L. & Cummins, C. C. Diuranium inverted sandwiches involving naphthalene and cyclooctatetraene. J. Am. Chem. Soc. 124, 7660-7661 (2002). (Pubitemid 34733770)
27. Evans, W. J., Kozimor, S. A., Ziller, J. W. & Kaltsoyannis, N. Structure, reactivity, and density functional theory analysis of the six-electron reductant, [(C5Me5)2U]2(m-Z6:Z6-C6H6), synthesized via a new mode of (C5Me5)3M reactivity. J. Am. Chem. Soc. 126, 14533-14547 (2004).
28. Evans, W. J., Traina, C. A. & Ziller, J. W. Synthesis of heteroleptic uranium (m-Z6:Z6-C6H6)2-sandwich complexes via facile displacement of (C5Me5)1-by ligands of lower hapticity and their conversion to heteroleptic bis(imido) compounds. J. Am. Chem. Soc. 131, 17473-17481 (2009).
29. Mills, D. P. et al. A delocalized arene-bridged diuranium single-molecule magnet. Nat. Chem. 3, 454-460 (2011).
30. Monreal, M. J., Khan, S. I., Kiplinger, J. L. & Diaconescu, P. L. Molecular quadrangle formation from a diuranium m-Z6:Z6-toluene complex. Chem. Commun. 47, 9119-9121 (2011).
31. Patel, D., Moro, F., McMaster, J., Lewis, W., Blake, A. J. & Liddle, S. T. A formal high oxidation state inverse-sandwich diuranium complex: a new route to f-block-metal bonds. Angew. Chem. Int. Ed. 50, 10388-10392 (2011).
32. Diaconescu, P. L. & Cummins, C. C. m-Z6:Z6-Arene-bridged diuranium hexakisketimide complexes isolable in two states of charge. Inorg. Chem. 51, 2902-2916 (2012).
33. Arnold, P. L., Mansell, S. M., Maron, L. & McKay, D. Spontaneous reduction and C-H borylation of arenes mediated by uranium(III) disproportionation. Nat. Chem. 4, 668-674 (2012).
34. Mougel, V. et al. Siloxides as supporting ligands in uranium(III)- mediated small-molecule activation. Angew. Chem. Int. Ed. 51, 12280-12284 (2012).
35. Patel, D. et al. A triamido-uranium(V) inverse-sandwich 10p-toluene tetraanion arene complex. Dalton Trans. 42, 5224-5227 (2013).
36. Vlaisavljevich, B., Diaconescu, P. L., Lukens, Jr W. L., Gagliardi, L. & Cummins, C. C. Investigations of the electronic structure of arene-bridged diuranium complexes. Organometallics 32, 1341-1352 (2013).
37. Haskel, A., Straub, T., Dash, A. K. & Eisen, M. S. Oligomerization and crossoligomerization of terminal alkynes catalyzed by organoactinide complexes. J. Am. Chem. Soc. 121, 3014-3024 (1999). (Pubitemid 29189746)
38. Haskel, A., Wang, J. Q., Straub, T., Neyroud, T. G. & Eisen, M. S. Controlling the catalytic oligomerization of terminal alkynes promoted by organoactinides: a strategy to short oligoners. J. Am. Chem. Soc. 121, 3025-3034 (1999). (Pubitemid 29189747)
39. Wang, J. Q., Dash, A. K., Berthet, J.-C., Ephritikhine, M. & Eisen, M. S. Selective dimerization of terminal alkynes promoted by the cationic actinide compound [(Et2N)3U][BPh4]. Formation of the alkyne p-complex [(Et2N)2U(C-CtBu)(Z2-HC-CtBu)][BPh4]. Organometallics 18, 2407-2409 (1999).
40. Wang, J., Kapon, M., Berthet, J.-C., Ephritikhine, M. & Eisen, M. S. Cross dimerization of terminal alkynes catalyzed by [(Et2N)3U][BPh4]. Inorg. Chim. Acta 334, 183-192 (2002).
41. Kosog, B., Kefalidis, C. E., Heinemann, F. W., Maron, L. & Meyer, K. Uranium(III)-mediated C-C-coupling of terminal alkynes: formation of dinuclear uranium(IV) vinyl complexes. J. Am. Chem. Soc. 134, 12792-12797 (2012).
42. Bertrand, G., Tortech, L., Fichou, D., Malacria, M., Aubert, C. & Gandon, V. An improved protocol for the synthesis of [(Z4-C4R4)Co(Z5-C5H5)] complexes. Organometallics 31, 126-132 (2012).
43. Cambridge Structural Database. CSD version 1.11, accessed 08/03/2013, http://cds.dl.ac.uk/cds/datasets/crys/csd/csd.html.
44. Berthet, J. C. & Ephritikhine, M. New advances in the chemistry of uranium amide compounds. Coord. Chem. Rev. 178-180, 83-116 (1998). (Pubitemid 128451194)
45. Frey, A. S. P., Cloke, F. G. N., Hitchcock, P. B. & Green, J. C. Activation of P4 by U(Z5-C5Me5)(Z8-C8H6(SiiPr3)2-1,4)(THF); the X-ray structure of [U(Z5-C5Me5)(Z8-C8H6(SiiPr3)2-1,4)]2(m-Z2:Z2-P4). N. J. Chem. 35, 2022-2026 (2011).
46. Stephens, F. H. PhD Thesis, Massachusetts Institute of Technology (2004).
47. Baudry, D., Ephritikhine, M., Nief, F., Ricard, L. & Mathey, F. Synthesis of phospholyltetrahydroboratouranium complexes. Crystal Structure of [(Z5-C4Me4P)2U(BH4)2]. Angew. Chem. Int. Ed. 29, 1485-1486 (1990).
48. Castro-Rodrguez, I. & Meyer, K. Small molecule activation at uranium coordination complexes: control of reactivity via molecular architecture. Chem. Commun. 1353-1368 (2006).
49. Lam, O. P., Heinemann, F. W. & Meyer, K. Activation of elemental S, Se and Te with uranium(III): bridging U-E-U (ES, Se) and diamond-core complexes U-(E)2-U (EO, S, Se, Te). Chem. Sci. 2, 1538-1547 (2011).
50. Gardner, B. M. et al. Homologation and functionalization of carbon monoxide by a recyclable uranium complex. Proc. Natl Acad. Sci. USA 109, 9265-9270 (2012).
51. Morris, D. E., Da Re, R. E., Jantunen, K. C., Castro-Rodriguez, I. & Kiplinger, J. L. Trends in electronic structure and redox energetics for early-actinide pentamethylcyclopentadienyl complexes. Organometallics 23, 5142-5153 (2004).
52. Cooper, O. J. et al. Uranium-Carbon Multiple Bonding: Facile Access to the Pentavalent Uranium Carbene [U{C(PPh2NSiMe3)2}(Cl)2(I)] and Comparison of UVC and UIVC Double Bonds. Angew. Chem. Int. Ed. 50, 2383-2386 (2011).
53. Mills, D. P. et al. Synthesis of a uranium(VI)-carbene: reductive formation of uranyl(V)-methanides, oxidative preparation of a [R2CUO]2\+ analogue of the [OUO]2\+ uranyl ion (RPh2PNSiMe3), and comparison of the nature of UIVC, UVC, and UVIC double bonds. J. Am. Chem. Soc. 134, 10047-10054 (2012).
54. King, D. M. et al. Isolation and characterization of a uranium(VI)-nitride triple bond. Nat. Chem. 5, 482-488 (2013).
55. Streitwieser, Jnr A. et al. Preparation and properties of uranocene, di-pcyclooctatetraeneuranium( IV). J. Am. Chem. Soc. 95, 8644-8649 (1973).
56. Seyferth, D. Uranocene. The first member of a new class of organometallic derivatives of the f elements. Organometallics 23, 3562-3583 (2004).
57. Fonseca-Guerra, C., Snijders, J. G., Velde, G. &, Baerends, E. J. Towards an order-N DFT method. Theor. Chem. Acc. 99, 391-403 (1998).
58. Velde, G. et al. Chemistry with ADF. J. Comput. Chem. 22, 931-967 (2001).
59. Gorelsky, S. I. AOMix: Program for Molecular Orbital Analysis; version 6.8 (University of Ottawa, 2013) http://www.sg-chem.net/.
60. Gorelsky, S. I. & Lever, A. B. P. Electronic structure and spectra of ruthenium diimine complexes by density functional theory and INDO/S. Comparison of the two methods. J. Organomet. Chem 635, 187-196 (2001). (Pubitemid 33618338)