Assembly of macrocycles by zirconocene-mediated, reversible carbon-carbon bond formation

Accounts of Chemical Research

Volumn 44, Issue 6, 2011, Pages 435-446

  Gessner, Viktoria H ^a   Tannaci, John F ^a   Miller, Adam D ^a   Tilley, T Don ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79959441767     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar100148g     Document Type: Article

References (84)

1. For review, see: Fyfe, M. C. T.; Stoddart, J. F. Synthetic Supramolecular Chemistry Acc. Chem. Res. 1997, 30, 393-401
2. Lehn, J.-M. Perspectives in Supramolecular Chemistry-From Molecular Recognition towards Molecular Information Processing and Self-Organization Angew. Chem., Int. Ed. Engl. 1990, 29, 1304-1319
3. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Molecular Encapsulation Angew. Chem., Int. Ed. 2002, 41, 1488-1508
4. Lehn, J.-M. Supramolecular Chemistry; VCH: New York, 1995.
5. Vögtle, F. Supramolecular Chemistry; Wiley: Chichester, U.K., 1991.
6. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Functional Molecular Flasks: New Properties and Reactions within Self-Assembled Hosts Angew. Chem., Int. Ed. 2009, 48, 3418-3438
7. Vigato, P. A.; Tamburini, S. The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives Coord. Chem. Rev. 2004, 248, 1717-2128
8. Borisova, N. E.; Reshetova, M. D.; Ustynyuk, Y. A. Metal-Free Methods in the Synthesis of Macrocyclic Schiff Bases Chem. Rev. 2007, 107, 46-79 (Pubitemid 46223701)
9. MacLachlan, M. J. Conjugated Shape-Persistent Macrocycles via Schiff-Base Condensation: New Motifs for Supramolecular Chemistry Pure Appl. Chem. 2006, 78, 873-888
10. Grubbs, R. H.; Chang, S. Recent Advances in Olefin Metathesis and Its Application in Organic Synthesis Tetrahedron 1998, 54, 4413-4450 (Pubitemid 28194778)
11. Host-Guest Complex Chemistry: Synthesis, Structure, Applications Vögtle, F.; Weber, E., Eds.; Springer-Verlag: Berlin, 1985.
12. Parker, D. Macrocycle Synthesis: A Practical Approach; Oxford University Press: Oxford, 1996.
13. For reviews, see: Negishi, E. Controlled Carbometallation as Tool for Carbon-Carbon Bond Formation and Its Application to Cyclization Acc. Chem. Res. 1987, 20, 65-72
14. Buchwald, S. L.; Nielsen, R. B. Group 4 Metal Complexes of Benzynes, Cycloalkynes, Acyclic Alkynes, and Alkenes Chem. Rev. 1988, 88, 1047-1058
15. Negishi, E.; Takahashi, T. Pattern of Reactions of Organozirconium and Related Complexes Acc. Chem. Res. 1994, 27, 124-130
16. Rosenthal, U.; Pellny, P.-M.; Kirchbauer, F. G.; Burlakov, V. V. What Do Titano- and Zirconocenes Do with Diynes and Polyynes? Acc. Chem. Res. 2000, 33, 119-129
17. Barluenga, J.; Rodrguez, F.; Álvarez-Rodrigo, L.; Fañanás, F. J. Coupling Reactions of Zirconocene Complexes and Heterosubstituted Alkenes Chem. Soc. Rev. 2005, 34, 762-768 (Pubitemid 41306028)
18. Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of Heterocycles J. Am. Chem. Soc. 1994, 116, 1880-1889 (Pubitemid 24980667)
19. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Reaction of Zirconocene Dichloride with Alkyllithiums or Alkyl Grignard Reagents As Method for Generating a "Zirconocene" Equivalant and Its Use in Zirconium-Promoted Cyclization Tetrahedron Lett. 1986, 27, 2829-2832
20. Mao, S. S. H.; Tilley, T. D. Polymers with Linked Macrocyclic Rings in the Main Chain. Zirconocene Coupling of 1,8-Cyclotetradecadiyne Macromolecules 1996, 29, 6362-6364 (Pubitemid 126544844)
21. 3) J. Organomet. Chem. 1996, 521, 425-428 (Pubitemid 126160948)
22. Mao, S. S. H.; Tilley, T. D. A Versatile, Transition-Metal Mediated Route to Blue-Light-Emitting Polymers with Tunable Luminescent Properties Macromolecules 1997, 30, 5566-5569
23. Lucht, B. L.; Buretea, M. A.; Tilley, T. D. Poly(2,5-diphenylgermole): Incorporation of a Germole Ring into a Conjugated Polymer Organometallics 2000, 19, 3469-3475
24. Lucht, B. L.; Mao, S. S. H.; Tilley, T. D. A Zirconocene-Coupling Route to Substituted Poly(p-phenylenedienylene)s: Band Gap Tuning via Conformational Control J. Am. Chem. Soc. 1998, 120, 4354-4365 (Pubitemid 28261195)
25. Suh, M. C.; Jiang, B. W.; Tilley, T. D. Efficient Synthetic Route to Oligomers Based on Zirconocene Coupling: Properties for Phenylene - Thiophene-1-Oxide and Phenylene - Thiophene-1,1-Dioxide Chains Angew. Chem., Int. Ed. 2000, 39, 2870-2873 (Pubitemid 30663807)
26. Nugent, W. A.; Thorn, D. L.; Harlow, R. L. Cyclization of Diacetylenes to Exocyclic Dienes. Complementary Procedures Based on Titanium and Zirconium Reagents J. Am. Chem. Soc. 1987, 109, 2788-2796
27. Erker, G.; Zwettler, R.; Kruger, C.; Hyla-Kryspin, I.; Gleiter, R. Reactions of β-CH Agostic Alkenylzirconocene Complexes Organometallics 1990, 9, 524-530
28. 2-Phenyltrimethyl-silylacetylene)zirconocene J. Organomet. Chem. 1991, 409, 179-188
29. 2) C≡CMe J. Am. Chem. Soc. 1995, 117, 5365-5366
30. 3 Unsaturated Macrocycles J. Am. Chem. Soc. 1995, 117, 7031-7032
31. Ben-Haida, A.; Baxter, I.; Colquhoun, H. M.; Hodge, P.; Kohnke, F. H.; William, D. J. Ring-Closing Depolymerisation of Aromatic Polyethers Chem. Commun. 1997, 1533-1534 (Pubitemid 127495424)
32. Ercolani, G.; Mandolini, L.; Mencarelli, P.; Roelens, S. Macrocyclization under Thermodynamic Control. A Theoretical Study and Its Application to the Cyclooligomerization of β-Propiolactone J. Am. Chem. Soc. 1993, 115, 3901-3908
33. Hubbard, P. A.; Brittain, W. J.; Mattice, W. L.; Brunelle, D. J. Ring-Size Distribution in the Depolymerization of Poly(butylene Terephthalate) Macromolecules 1998, 31, 1518-1522 (Pubitemid 128587220)
34. Youk, J. H.; Kambour, R. P.; MacKnight, W. J. Preparation and Polymerization of Ethylene 2,6-Naphthalenedicarboxylate Cyclic Oligomers Macromolecules 2000, 33, 3606-3610
35. For examples, see: Mohr, B.; Weck, M.; Sauvage, J.-P.; Grubbs, R. H. High-Yield Synthesis of Catenanes by Intramolecular Ring-Closing Metathesis Angew. Chem., Int. Ed. Engl. 1997, 36, 1308-1310
36. Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Approach to Epothilones Based on Olefin Metathesis Angew. Chem., Int. Ed. Engl. 1996, 35, 2399-2401
37. Guo, J.; Mayers, P. C.; Breault, G. A.; Hunter, C. A. Synthesis of a Molecular Trefoil Knot by Folding and Closing on an Octahedral Coordination Template Nat. Chem. 2010, 2, 218-222
38. Fürstner, A.; Seidel, G. Ring-Closing Metathesis of Functionalized Acetylene Derivatives: New Entry into Cycloalkynes Angew. Chem., Int. Ed. 1998, 37, 1734-1736 (Pubitemid 28348561)
39. Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry; VCH: Weinheim, New York, 1993.
40. Suginome, M.; Oike, H.; Shuff, P. H.; Ito, Y. Synthesis of Organosilicon Macrocycles. Palladium-Catalyzed Ring-Enlargement Oligomerization of Cyclic Disilanes via Si-Si σ-Bond Metathesis Organometallics 1996, 15, 2170-2178
41. Brady, P. A.; Bonar-Law, R. P.; Rowan, S. J.; Suckling, C. J.; Sanders, J. K. M. 'Living' Macrolactonisation: Thermodynamically-Controlled Cyclisation and Interconversion of Oligocholates J. Chem. Soc., Chem. Commun. 1996, 319-320
42. Pschirer, N. G.; Fu, W.; Adams, R. D.; Bunz, U. H. F. Ring-Closing Alkyne Metathesis with Simple Catalyst Systems: Access to Molecular Triangles and Rhomboids Chem. Commun. 2000, 87-88 (Pubitemid 30066900)
43. Hara, R.; Xi, Z. F.; Kotora, M.; Xi, C. J.; Takahashi, T. Substituent-Dependent Selective Replacement of Alkyne Moieties of Zirconacyclopentadienes via C-C Bond Cleavage Reaction Chem. Lett. 1996, 1003-1004
44. Miller, A. D.; Johnson, S. A.; Tupper, K. A.; McBee, J. L.; Tilley, T. D. Unsymmetrical Zirconacyclopentadienes from Isolated Zirconacyclopropenes with 1-Alkynylphosphine Ligands Organometallics 2009, 28, 1252-1262
45. Johnson, S. A.; Liu, F.-Q.; Suh, M. C.; Zürcher, S.; Haufe, M.; Mao, S. S. H.; Tilley, T. D. Regioselective coupling of Pentafluorophenyl Substituted Alkynes: Mechanistic Insight into Zirconocene Coupling of Alkynes and Facile Route to Conjugated Polymers Bearing Electron-Withdrawing Substituents J. Am. Chem. Soc. 2003, 125, 4199-4211 (Pubitemid 36512314)
46. Miller, A. D.; Tannaci, J. F.; Johnson, S. A.; Lee, H.; McBee, J. L.; Tilley, T. D. Mesityl Alkyne Substituents for Control of Regiochemistry and Reversibility in Zirconocene Couplings: New Synthetic Strategies for Unsymmetrical Zirconacyclopentadienes and Conjugated Polymers J. Am. Chem. Soc. 2009, 131, 4917-4927
47. Buchwald, S. L.; Nielsen, R. B. Selective, Zirconium-Mediated Cross-Coupling of Alkynes: Synthesis of Isomerically Pure 1,3-Dienes and 1,4-Diiodo 1,3-Dienes J. Am. Chem. Soc. 1989, 111, 2870-2874
48. 3)- Mediated Coupling Reactions of Acetylenes (M = Ni, Pt). Significant Differences between Early and Late-Transition-Metal Complexes Organometallics 2005, 24, 2129-2140 (Pubitemid 40644092)
49. Buchwald, S. L.; Watson, B. T.; Huffman, J. C. Synthesis, Reactions, and Molecular Structure of Zirconocene-Alkyne Complexes J. Am. Chem. Soc. 1987, 409, 2544-2546
50. Takahashi, T.; Swanson, D. R.; Negishi, E. Zirconacyclopropanes and Zirconacyclopropenes. Synthesis, Characterization and Reactions Chem. Lett. 1987, 623-626
51. Miller, A. D.; McBee, J. L.; Tilley, T. D. Mechanism of Reversible Alkyne Coupling at Zirconocene: Ancillary Ligand Effects J. Am. Chem. Soc. 2008, 130, 4992-4999 (Pubitemid 351500133)
52. Takahashi, T.; Kotora, M.; Hara, R.; Xi, Z. Carbon-Carbon Bond Cleavage and Selective Transformation of Zirconacycles Bull. Chem. Soc. Jpn. 1999, 72, 2591-2602 (Pubitemid 30007354)
53. Warner, B. P.; Davis, W. M.; Buchwald, S. L. Synthesis and X-ray Structure of a Zirconocene Complex of Two Alkynes J. Am. Chem. Soc. 1994, 116, 5471-5472 (Pubitemid 24981134)
54. Mao, S. S. H.; Liu, F. Q.; Tilley, T. D. Efficient Zirconocene-Coupling of Silicon-Substituted Diynes to Polymers and Macrocycles J. Am. Chem. Soc. 1998, 120, 1193-1206 (Pubitemid 28179035)
55. Schafer, L. L.; Nitschke, J. R.; Mao, S. S. H.; Liu, F.-Q.; Harder, G.; Haufe, M.; Tilley, T. D. Zirconocene-Mediated, High-Yielding Macrocyclizations of Silyl-Terminated Diynes Chem.-Eur. J. 2002, 8, 74-83 (Pubitemid 34087369)
56. For review, see: Moore, J. S. Shape-Persistent Molecular Architectures of Nanoscale Dimension Acc. Chem. Res. 1997, 30, 402-413 (Pubitemid 127472591)
57. Grave, C.; Schlüter, A. D. Shape-Persistent, Nano-Sized Macrocycles Eur. J. Org. Chem. 2002, 3075-3098
58. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Polyethynylated Cyclic π-Systems: Scaffoldings for Novel Carbon Networks Chem. Soc. Rev. 1999, 28, 107-119
59. Nitschke, J. R.; Tilley, T. D. Efficient, High-Yield Route to Long, Functionalized p -Phenylene Oligomers Containing Perfluorinated Segments, and Their Cyclodimerizations by Zirconocene Coupling J. Am. Chem. Soc. 2001, 123, 10183-10190 (Pubitemid 32979766)
60. 3) Z. Anorg. Allg. Chem. 1995, 621, 77-83
61. Nitschke, J.; Tilley, T. D. Bipyridine-Containing Cyclophanes via Zirconocene Coupling J. Org. Chem. 1998, 63, 3673-3676 (Pubitemid 128494497)
62. Nitschke, J. R.; Zurcher, S.; Tilley, T. D. New Zirconocene-Coupling Route to Large, Functionalized Macrocycles J. Am. Chem. Soc. 2000, 122, 10345-10352
63. Nitschke, J.; Tilley, T. D. Novel Templating Effect in the Macrocyclization of Functionalized Diynes by Zirconocene Coupling Angew. Chem., Int. Ed. 2001, 40, 2142-2145 (Pubitemid 33644343)
64. Lucht, B. L.; Tilley, T. D. Zirconocene-Coupling Routes to Conjugated Polymers: Soluble Poly(arylenedienylene)s Chem. Commun. 1998, 1645-1646 (Pubitemid 128675729)
65. For examples, see: Takahashi, T.; Kotora, M.; Xi, Z. F. Cycloaddition of Zirconacyclopentadienes to Alkynes Using Copper Salts: Formation of Benzene Derivatives J. Chem. Soc., Chem. Commun. 1995, 361-362
66. Takahashi, T.; Ishikawa, M.; Huo, S. Q. Reaction of a Double Bond of Zirconacyclopentadienes: Formation of 1,2,3,5-Tetrasubstituted Benzenes J. Am. Chem. Soc. 2002, 124, 388-389 (Pubitemid 34084130)
67. Kotora, M.; Xi, C.; Takahashi, T. Cross Coupling-Conjugate Addition of Zirconacyclopentadienes with 3-Iodopropenoates Tetrahedron Lett. 1998, 39, 4321-4324 (Pubitemid 28240054)
68. Takahashi, T.; Xi, C.; Kotora, M. 1,1-Cycloaddition of Zirconacyclopentadienes to Propynoates Chem. Commun. 1997, 2069-2070 (Pubitemid 127696217)
69. Takahashi, T.; Li, Y.; Ito, T.; Xu, F.; Nakajima, K.; Liu, Y. Reactions of Zirconacyclopentadienes with CO, CN, and NN Moieties with Electron-Withdrawing Groups: Formation of Six-Membered Heterocycles J. Am. Chem. Soc. 2002, 124, 1144-1145 (Pubitemid 34169102)
70. Fagan, P. J.; Nugent, W. A. Synthesis of Main Group Heterocycles by Metallacycle Transfer from Zirconium J. Am. Chem. Soc. 1988, 110, 2310-2312
71. Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. Silole Derivatives as Efficient Electron Transporting Materials J. Am. Chem. Soc. 1996, 118, 11974-11975 (Pubitemid 26417496)
72. Uchida, M.; Izumizawa, T.; Nakano, T.; Yamaguchi, S.; Tamao, K.; Furukawa, K. Structural Optimization of 2,5-Diarylsiloles as Excellent Electron-Transporting Materials for Organic Electroluminescent Devices Chem. Mater. 2001, 13, 2680-2683 (Pubitemid 32830726)
73. Hay, C.; Hissler, M.; Fischmeister, C.; Rault-Berthelot, J.; Toupet, L.; Nyulaszi, L.; Reau, R. Phosphole Containing π-Conjugated Systems: From Model Molecules to Polymer Film on Electrodes Chem.-Eur. J. 2001, 7, 4222-4236 (Pubitemid 32971319)
74. Nakamoto, M.; Tilley, T. D. Reactions of Zirconacyclopentadienes with Nitrosobenzene. Characterization of Zirconacycle Intermediates and Formation of N -Phenylpyrroles Organometallics 2001, 20, 5515-5517 (Pubitemid 35349116)
75. Jiang, B.; Tilley, T. D. General, Efficient Route to Thiophene-1-Oxides and Well-Defined, Mixed Thiophene-Thiophene-1-Oxide Oligomers J. Am. Chem. Soc. 1999, 121, 9744-9745 (Pubitemid 29498507)
76. Nitschke, J. R.; Tilley, T. D. Convenient, Zirconocene-Coupling Routes to Germole- And Thiophenecontaining Macrocycles with Triangular Geometries J. Organomet. Chem. 2003, 666, 15-22 (Pubitemid 36105343)
77. Tejeda, A.; Oliva, A. I.; Simon, L.; Grande, M.; Caballero, M. C.; Moran, J. R. A Macrocyclic Receptor for Chiral Recognition of Hydroxycarboxylates Tetrahedron Lett. 2000, 41, 4563-4566 (Pubitemid 30407713)
78. Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors Chem. Rev. 1997, 97, 3313-3362
79. Gross, Z.; Ini, S. Asymmetric Catalysis by a Chiral Ruthenium Porphyrin: Epoxidation, Hydroxylation, and Partial Kinetic Resolution of Hydrocarbon Org. Lett. 1999, 1, 2077-2080
80. Collman, J. P.; Wang, Z.; Strausmanis, A.; Quelquejeu, M. Efficient Catalyst for Asymmetric Epoxidation of Terminal Olefins J. Am. Chem. Soc. 1999, 121, 460-461 (Pubitemid 29060977)
81. Groves, J. T.; Viski, P. Asymmetric Hydroxylation, Epoxidation, and Sulfoxidation Catalyzed by Vaulted Binaphthyl Metalloporphyrins J. Org. Chem. 1990, 55, 3628-3634
82. Schafer, L. L.; Tilley, T. D. Efficient Diastereoselective Syntheses of Chiral Macrocycles via Zirconocene Coupling. Synthetic Control of Size and Geometry J. Am. Chem. Soc. 2001, 123, 2683-2684 (Pubitemid 32888577)
83. Tannaci, J. F.; Kratter, I. H.; Rider, E. A.; McBee, J. L.; Miller, A. D.; Tilley, T. D. Stereoselective Macrocyclization through Zirconocene-Mediated Coupling of Achiral Dialkynes Chem. Commun. 2009, 233-234
84. Liu, F. Q.; Harder, G.; Tilley, T. D. A Simple, Efficient Route to Cage Compounds via Zirconocene Coupling J. Am. Chem. Soc. 1998, 120, 3271-3272