Stimuli-responsive olefin metathesis catalysts

Current Organic Chemistry

Volumn 17, Issue 22, 2013, Pages 2575-2591

  Schanz, Hans Jörg ^a  

^a GEORGIA SOUTHERN UNIVERSITY   (United States)

Author keywords

Olefin metathesis; Organic synthesis; Polymerization; Reaction control; Ruthenium

Indexed keywords

FUNCTIONAL POLYMERS; OLEFINS; RUTHENIUM COMPOUNDS;

ALKYLIDENE COMPLEXES; CATALYST DESIGNS; METATHESIS ACTIVITY; METATHESIS CATALYSTS; OLEFIN METATHESIS; ORGANIC SYNTHESIS; REACTION CONTROL; STIMULI-RESPONSIVE; SYNTHETIC TECHNOLOGY; ]+ CATALYST;

CATALYSTS;

EID: 84893165957     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990110     Document Type: Article

References (186)

1. Grubbs, R.H.; Ed., Handbook of Metathesis, Wiley-VCH, Weinheim, 2003, Vol 1-3.
2. Nuyken, O.; Schneider, M.; Frenzel, U. Metathesis Polymerization. Encyclopedia of Polymer Science and Technology, Wiley, New York, NY, USA, 2012.
3. Leitgelb, A.; Wappel, J.; Slugovc, C. The ROMP Toolbox Upgraded. Polymer 2010, 51, 2927-2946.
4. Bielawski, C.W.; Grubbs, R.H. Living Ring-Opening Metathesis Polymerization. Prog. Polym. Sci. 2007, 32, 1-29.
5. Baughman, T.W.; Wagener, K.B. Recent Advances in ADMET Polymerization, Metathesis Polymerization. Adv. Polym. Sci. 2005, 176, 1-42.
6. Trimmel, G., Riegler, S., Fuchs, G., Slugovc, C., Stelzer, F. Liquid Crystalline Polymers by Metathesis Polymerization. Adv. Polym. Sci. 2005, 176, 43-87.
7. Conrad, J.C.; Fogg, D.E. Ruthenium-Catalyzed Ring-Closing Metathesis: Advances, Limitations, and Opportunities. Curr. Org. Chem. 2006, 10, 185-202.
8. Chatterjee, A.K.; Choi, T.-L.; Sanders, D.P.; Grubbs, R.H. A General Model for Selectivity in Olefin Cross Metathesis. J. Am. Chem. Soc. 2003, 125, 11360-11370.
9. Wright, D.L. Application of Olefin Metathesis to Organic Synthesis. Curr. Org. Chem. 1999, 3, 211-240.
10. Chauvin, Y. Olefin Metathesis: The Early Days (Nobel Lecture) Angew. Chem. Int. Ed. 2006, 45, 3748-3759.
11. Schrock, R.R. Multiple Metal-Carbon Bonds for Catalytic Metathesis Reactions (Nobel Lecture) Angew. Chem. Int. Ed. 2006, 45, 3748-3759.
12. Grubbs, R.H. Olefin-Metathesis Catalysts for the Preparation of Molecules and Materials (Nobel Lecture). Angew. Chem. Int. Ed. 2006, 45, 3760-3765.
13. Sanford, M.S.; Love, J.L.; Grubbs, R.H. Mechanism and Activity of Ruthenium Olefin Metathesis Catalysts. J. Am. Chem. Soc. 2001, 123, 6543-6554.
14. Dias, E.L.; Nguyen, S.T.; Grubbs, R.H. Well-Defined Ruthenium Olefin Metathesis Catalysts: Mechanism and Activity. J. Am. Chem. Soc. 1997, 119, 3887-3897.
15. Rouhi, A.M. Olefin Metathesis: Big Deal Reaction. Chem. Eng. News 2002, 80, 34-38.
16. Calderon, N.; Chen, H.; Scott, K.W. Olefin Metathesis A Novel. Reaction for Skeletal Transformations of Unsaturated Hydrocarbons. Tetrahedron Lett. 1967, 8, 3327-3329.
17. Calderon, N. Olefin Metathesis Reaction. Acc. Chem. Res. 1972, 5, 127-132.
18. Herrison, J.L.; Chauvin, Y. Catalysis of Olefin Transformations by Tungsten Complexes. II. Telomerization of Cyclic Olefins in the Presence of Acyclic Olefins. Makromol. Chem. 1971, 141, 161-176.
19. Katz, T.J.; McGinnis, J. Mechanism of the Olefin Metathesis Reaction. J. Am. Chem. Soc. 1975, 97, 1592-1594.
20. Katz, T.J.; Rothschild, R. Mechanism of Olefin Metathesis of 2,2'-Divinylbiphenyl. J. Am. Chem. Soc. 1976, 98, 2519-2526.
21. Tebbe, F.N.; Parcshall, G.W.; Reddy, G.S. Olefin Homologation with Titanium Methylene Compounds. J. Am. Chem. Soc. 1978, 100, 3611-3613.
22. Schrock, R.R. First Isolable Transition Metal Methylene Complex and Analogs. Characterization, Mode of Decomposition, and Some Simple Reactions. J. Am. Chem. Soc. 1975, 97, 6577-6578.
23. Wood, C.D.; McLain, S.J.; Schrock, R.R. Multiple Metal-Carbon Bonds. 13. Preparation and Characterization of Monocyclopentadienyl Mononeopentylidene Complexes of Niobium and Tantalum Including the first Details of an a-Abstraction Process. J. Am. Chem. Soc. 1979, 101, 3210-3222.
24. Wallace, K.C.; Liu, A.H.; Dewan, J.C.; Schrock, R.H. Preparation and Reactions of Tantalum Alkylidene Complexes containing bulky Phenoxide or Thiolate Ligands. Controlling Ring-Opening Metathesis Polymerization Activity and Mechanism through Choice of anionic Ligand. J. Am. Chem. Soc. 1988, 110, 4964-4977.
25. Schrock, R.R.; Murdzek J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Reagan, M. Synthesis of Molybdenum Imido Alkylidene Complexes and some Reactions involving Acyclic Olefins. J. Am. Chem. Soc. 1990, 112, 3875-3886.
26. Bazan, G.C.; Oskam, J.H.; Cho, H.-N.; Park, L.Y.; Schrock, R.R. Living Ring-Opening Metathesis Polymerization of 2,3-Difunctionalized 7-Oxanorbornenes and 7-Oxanorbornadienes by Mo(CHCMe2R) (NC6H3-iso-Pr2-2,6)(O-tert-Bu)2 and Mo(CHCMe2R)(NC6H3-iso-Pr2-2,6)(OCMe2CF3)2. J. Am. Chem. Soc. 1991, 113, 6899-6907.
27. Aeilts, S.L.; Cefalo, D.R.; Bonitatebus, Jr., P.J.; Houser, J.H.; Hoveyda, A.H.; Schrock, R.R. A Readily Available and User-Friendly Chiral Catalyst for Efficient Enantioselective Olefin Metathesis. Angew. Chem. Int. Ed. 2001, 40, 1452-1456.
28. Katz, T.J.; Lee, S.J.; Acton, N. Metatheses Induced by (Phenylmethoxycarbene) pentacarbonyltungsten. Tetrahedron Lett. 1976, 17, 4251-4254.
29. Kress, J.; Wesolek, M.; Osborn, J.A. Tungsten (IV) Carbenes for the Metathesis of Olefins. Direct Observation and Identification of the Chain Carrying Carbene Complexes in a Highly Active Catalyst System. J. Chem. Soc., Chem. Commun. 1982, 514-516.
30. Kress, J.; Osborn, J.A. Tungsten Carbene Complexes in Olefin Metathesis: a Cationic and Chiral Active Species. J. Am. Chem. Soc. 1983, 105, 6346-6347.
31. Kress, J.; Aguero, A; Osborn, J. A. Recent Advances in the Chemistry of Tungsten-Carbene Complexes. J. Mol. Catal. 1986, 36, 1-12.
32. Schaverien, C. J.; Dewan, J. C; Schrock, R. R. Multiple Metal-Carbon Bonds. 43. Well-Characterized, Highly Active, Lewis Acid Free Olefin Metathesis Catalysts. J. Am. Chem. Soc. 1986, 108, 2771-2773.
33. Nguyen, S.T.; Johnson, L.K.; Grubbs, R.H.; Ziller, J.W. Ring-Opening Metathesis Polymerization (ROMP) of Norbornene by a Group VIII Carbene Complex in Protic Media. J. Am. Chem. Soc. 1992, 114, 3974-3975.
34. Nguyen, S.T.; Grubbs, R.H. Syntheses and Activities of New Single-Component, Ruthenium-Based Olefin Metathesis Catalysts. J. Am. Chem. Soc. 1993, 115, 9858-9859.
35. Schwab, P.; Grubbs, R.H.; Ziller, J.W. A Series of Well-Defined Metathesis Catalysts-Synthesis of [RuCl2(=CHR') (PR3)2] and its Reactions. Angew.Chem. Int. Ed. 1995, 34, 2039-2041.
36. Schwab, P.; Grubbs, R.H.; Ziller, J.W. Synthesis and Applications of RuCl2(=CHR')(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity. J. Am. Chem. Soc. 1996, 118, 100-110.
37. Grubbs, R.H. Introduction. Handbook of Metathesis, Grubbs, R.H. (eds.), Wiley-VCH, Weinheim, 2003, Vol. 1, 1-3.
38. Lynn, D.M.; Mohr, B.; Grubbs, R.H.; Henling, L.M.; Day, M.W. Water-Soluble Ruthenium Alkylidenes: Synthesis, Characterization, and Application to Olefin Metathesis in Protic Solvents. J. Am. Chem. Soc. 2000, 122, 6601-6609.
39. Lynn, D.M.; Mohr, B.; Grubbs, R.H. Living Ring-Opening Metathesis Polymerization in Water. J. Am. Chem. Soc. 1998, 116, 1627-1628.
40. Mohr, B.; Lynn, D.M.; Grubbs, R.H. Synthesis of Water-Soluble, Aliphatic Phosphines and Their Application to Well-Defined Ruthenium Olefin Metathesis Catalysts. Organometallics 1996, 15, 4317-4325.
41. Gallivan, J.P.; Jordan, J.P.; Grubbs, R.H. A Neutral, Water-Soluble Olefin Metathesis Catalyst Based on an N-Heterocyclic Carbene Ligand. Tetrahedron Lett. 2005, 46, 2577-2580.
42. Hong, S.H.; Grubbs, R.H. Highly Active Water-Soluble Olefin Metathesis Catalyst. J. Am. Chem. Soc. 2006, 128, 3508-3509
43. Jordan, J.P.; Grubbs, R.H. Small-Molecule N-Heterocyclic-Carbene-Containing Olefin-Metathesis Catalysts for Use in Water. Angew. Chem. Int. Ed. 2007, 46, 5152-5155.
44. Gulajski, L.; Michrowska, A.; Naroznik, J.; Kaczmarska, Z.; Rupnicki, L.; Grela, K. A Highly Active Aqueous Olefin Metathesis Catalyst Bearing a Quaternary Ammonium Group. Chem-SusChem 2008, 1, 1-8.
45. Vougiokalakis, G.C.; Grubbs, R.H. Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts. Chem. Rev. 2010, 110,1746-1787.
46. Samojlowicz, C.; Bieniek, M.; Grela, K. Ruthenium-Based Olefin Metathesis Catalysts Bearing N-Heterocyclic Carbene Ligands. Chem. Rev. 2009, 109, 3708-3742.
47. Colacino, E.; Martinez, J.; Lamaty, F. Preparation of NHC-Ruthenium Complexes and their Catalytic Activity in Metathesis Reaction. Coord. Chem. Rev. 2007, 251, 726-764.
48. Huang, J.; Schanz, H.-J.; Stevens, E.D.; Nolan, S.P. Influence of Sterically Demanding Carbene Ligation on Catalytic Behavior and Thermal Stability of Ruthenium Olefin Metathesis Catalysts. Organometallics 1999, 18, 5375-5380.
49. Huang J.; Stevens, E.D.; Nolan, S.P.; Peterson, J.L. Olefin Metathesis-Active Ruthenium Complexes Bearing a Nucleophilic Carbene Ligand. J. Am. Chem. Soc. 1999, 121, 2674-2678.
50. Scholl, M.; Ding, S.; Lee, C.W.; Grubbs, R.H. Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligand. Org. Lett. 1999, 1, 953-956.
51. Bielawski, C.W., Grubbs, R.H. Highly Efficient Ring Opening Metathesis Polymerization (ROMP) Using New Ruthenium Catalysts Containing N-Heterocyclic Carbene Ligands. Angew. Chem. Int. Ed. 2000, 39, 2903-2906.
52. Hoveyda, A.H.; Zhugralin, A.R. The Remarkable Metal-Catalysed Olefin Metathesis Reaction. Nature 2007, 450, 243-251.
53. Kingsbury, J.S.; Harrity, J.P.A.; Bonitatebus, P.J., Jr.; Hoveyda, A.H. A Recyclable Ru-Based Metathesis Catalyst J. Am. Chem. Soc. 1999, 121, 791-799.
54. Garber, S.B.; Kingsbury, J.S.; Gray, B.L.; Hoveyda, A.H. Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts. J. Am. Chem. Soc. 2000, 122, 8168-8179.
55. K Grela; Harutyunyan, S.; Michrowska, A. A Highly Efficient Ruthenium Catalyst for Metathesis Reactions. Angew. Chem. Int. Ed. 2002, 41, 4038-4040.
56. Van Veldhuizen, J.J.; Garber, S.B.; Kingsbury, J.S.; Hoveyda, A.H. A Recyclable Chiral Ru Catalyst for Enantioselective Olefin Metathesis. Efficient Catalytic Asymmetric Ring-Opening/Cross Metathesis in Air. J. Am. Chem. Soc. 2002, 124, 4954-4955.
57. Michrowska, A.; Gulajski, L.; Grela, K. A Simple and Practical Phase-Separation Approach to the Recycling of a Homogeneous Metathesis Catalyst. Chem. Commun. 2006, 841-843.
58. Gradillas, A.; Perez-Castells, J. Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations. Angew. Chem. Int. Ed. 2006, 45, 6086-6101.
59. Ulman, M.; Grubbs, R.H. Ruthenium Carbene-Based Olefin Metathesis Initiators: Catalyst Decomposition and Longevity. J. Org. Chem. 1999, 64, 7202-7207.
60. Chung, C.K.; Grubbs, R.H. Olefin Metathesis Catalysts: Stabilization Effect of Backbone Substitutions of N-Heterocyclic Carbene. Org. Lett. 2008, 10, 2693-2696.
61. Hong, S.H.; Chlenov, A.; Day, M.W.; Grubbs, R.H. Double C-H Activation of an N-Heterocyclic Carbene Ligand in a Ruthenium Olefin Metathesis Catalyst. Angew. Chem. Int. Ed. 2007, 46, 5148-5151.
62. Mathew, J.; Koga, N.; Suresh, C.H. C-H Bond Activation through σ-Bond Metathesis and Agostic Interactions. Deactivation Pathway of a Grubbs Second Generation Catalyst. Organometallics 2008, 27, 4666-4670.
63. Vehlow, K.; Gessler, S.; Blechert, S. Deactivation of Ruthenium Olefin Metathesis Catalysts through Intramolecular Carbene-Arene Bond Formation. Angew. Chem. Int. Ed. 2006, 45, 8082-8085.
64. Hong, S.H.; Day, M.W.; Grubbs, R.H. Decomposition of a Key Intermediate in Ruthenium-Catalyzed Olefin Metathesis Reactions. J. Am. Chem. Soc. 2004, 126, 7414-7415.
65. Hong, S.H.; Wenzel, A.G.; Salguero, T.T.; Day, M.W.; Grubbs, R.H. Prevention of Isomerization during Olefin Metathesis. J. Am. Chem. Soc. 2007, 129, 7961-7968.
66. Matyjaszewski, K. Ranking Living Systems. Macromolecules 1993, 26, 1787-1788.
67. Choi, T.-L.; Grubbs, R.H. Controlled Living Ring-Opening-Metathesis Polymerization by a Fast-Initiating Ruthenium Catalyst. Angew. Chem. Int. Ed. 2003, 42, 1743-1746.
68. Courchay, F.C.; Sworen, J.C.; Ghiviriga, I.; Abboud, K.A.; Wagener, K.B. Understanding Structural Isomerization during the Ruthenium-Catalyzed Olefin Metathesis: A Deuterium Labeling Study. Organometallics 2006, 25, 6074-6086.
69. Hong, S.H.; Sanders, D.P.; Lee, C.W.; Grubbs, R.H. Prevention of Undesirable Isomerization during Olefin Metathesis. J. Am. Chem. Soc. 2005, 127, 17160-17161.
70. Schmidt, B. Ruthenium-Catalyzed Olefin Metathesis Double-Bond Isomerization Sequence. J. Org. Chem. 2004, 69, 7672-7687.
71. Delaude, L.; Demonceau, A. Retracing the evolution of monometallic ruthenium-arene catalysts for C-C bond formation. Dalton Trans. 2012, 9257-9268.
72. Lozano-Vial, A.M.; Monsaert, S.; Bajek, A.; Verpoort, F. Ruthenium-Based Olefin Metathesis Catalysts Derived from Alkynes. Chem. Rev. 2010, 110, 4865-4909.
73. Diesendruck, C.E.; Tzur, E.; Lemcoff, N.G. The Versatile Alkylidene Moiety in Ruthenium Olefin Metathesis Catalyst. Eur. J. Inorg. Chem. 2009, 4185-4203.
74. Fürstner, A.; Hill, A.F.; Liebl, M.; Wilton-Ely, J.D.E.T. Coordinatively Unsaturated Ruthenium Allenylidene Complexes: Highly Effective, Well Defined Catalysts for the Ring-Closure Metathesis of α,ω-Dienes and Dienynes. Chem. Commun. 1999, 601-602.
75. Harlow, K.J.; Hill, A.F.; Wilton-Ely, J.D.E.T. The First Co-ordinatively Unsaturated Group-8 Allenylidene Complexes: Insights into Grubbs' vs. Dixneuf-Fürstner Olefin Metathesis Catalysts. J. Chem. Soc., Dalton Trans. 1999, 285-291. -The originally assigned allenylidene structure was later corrected
76. Jafarpour, L.; Schanz, H.-J.; Stevens, E.D.; Nolan, S.P. Indenylidene-Imidazolylidene Complexes of Ruthenium as Ring-Closing Metathesis Catalysts. Organometallics 1999, 18, 5416-5419.
77. Randl, S.; Gessler, S.; Wakamatsu, H.; Blechert, S. Highly Selective Cross Metathesis with Acrylonitrile Using a Phosphine Free Ru-Complex. Synlett 2001, 3, 430-432.
78. Burtscher, D.; Lexer, C.; Mereiter, K.; Winde, R.; Karch, R.; Slugovc, C. Controlled Living Ring-Opening Metathesis Polymerization with a Ruthenium Indenylidene Initiator. J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 4630-4635.
79. Bienik, M.; Michrowska, A.; Usanov, D.L.; Grela, K. In an Attempt to Provide a User's Guide to the Galaxy of Benzylidene, Alkoxybenzulidene, and Indenylidene Ruthenium Olefin Metathesis Catalysts. Chem. Eur. J. 2008, 14, 806-818.
80. Boeda, F.; Clavier, H.; Nolan, S.P. Ruthenium-Indenylidene Complexes: Powerful Tools for Metathesis Transformations. Chem. Commun. 2008, 2726-2740.
81. Dragutan, V; Dragutan, I.; Verpoort, F. Ruthenium Indenylidene Complexes Platinum Metals Rev. 2005, 49, 33-40.
82. de Fremont, P.; Clavier, H.; Montembault, V.; Fontaine, L.; Nolan, S.P. Ruthenium-Indenylidene Complexes in Ring Opening Metathesis Polymerization (ROMP) Reactions. J. Mol. Catal. A, Chem. 2008, 283, 108-113.
83. Clavier, H.; Nolan, S.P. N-Heterocyclic Carbene and Phosphine Ruthenium Indenylidene Precatakysts: A Comparative Study in Olefin Metathesis. Chem. Eur. J. 2007, 13, 8029-8036.
84. Zaman, S.; Curnow, O.J.; Abell, A.D. Development of Aqueous Metathesis Catalysts. Austr. J. Chem. 2009, 62, 91-100.
85. Burtscher, D.; Grela, K. Aqueous Olefin Metathesis. Angew. Chem. Int. Ed. 2009, 48, 442-454.
86. Binder, J.B.; Raines, R.T. Olefin Metathesis for Chemical Biology. Curr. Opin. Chem. Biol. 2008, 12, 767-773.
87. Stewart, I.C.; Ung, T.; Pletnev A.A.; Berlin, J.M.; Grubbs, R.H.; Schrodi, Y. Highly Efficient Ruthenium Catalysts for the Formation of Tetrasubstituted Olefins via Ring-Closing Metathesis. Org. Lett. 2007, 9, 1589-1592.
88. Berlin, J.M.; Campbell, K.; Ritter, T.; Funk, T.W.; Grubbs, R.H. Ruthenium-Catalyzed Ring-Closing Metathesis to Form Tetrasubstituted Olefins. Org. Lett. 2007, 9, 1339-1342.
89. Vougioukalakis, G.C. Removing Ruthenium Residues from Olefin Metathesis Reaction Products. Chem. Eur. J. 2012, 18, 8868-8880.
90. Clavier, H.; Grela, K.; Kirschning, A.; Mauduit, M.; Nolan, S.P. Sustainable Concepts in olefin Metathesis. Angew. Chem. Int. Ed. 2007, 46, 6786-6801.
91. Sledz, P.; Mauduit, M.; Grela, K. Olefin Metathesis in Ionic Liquids. Chem. Soc. Rev. 2008, 37, 2433-2442.
92. Coporet, C. Stereoselectivity of Supported Alkene Metathesis Catalysts: A Goal and a Tool to Characterize Active Sites. Beilstein J. Org. Chem. 2011, 76, 13-21.
93. Buchmeiser, M.R. Polymer-Supported Well-Defined Metathesis Catalysts. Chem. Rev. 2009, 109, 303-321.
94. Sommer, W.J., Weck, M. Supported N-Heterocyclic Carbene Complexes in Catalysis. Coord. Chem. Rev. 2007, 251, 860-873.
95. Herbert, M. B.; Marx, V.M.; Pederson, R.L.; Grubbs, R.H. Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis. Angew. Chem. Int. Ed. 2013, 52, 310-314.
96. Marx, V.M.; Herbert, M.B.; Keitz, B.K.; Grubbs, R.H. Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis. J. Am. Chem. Soc. 2013, 135, 94-97.
97. Keitz, B.K.; Endo, K.; Patel, P.R.; Herbert, M.B.; Grubbs, R.H. Improved Ruthenium Catalysts for Z-Selective Olefin Metathesis. J. Am. Chem. Soc. 2012, 134, 693-699.
98. Keitz, B.K.; Endo, K.; Herbert, M.B.; Grubbs, R.H. Z-Selective Homodimerization of Terminal Olefins with a Ruthenium Metathesis Catalyst. J. Am. Chem. Soc. 2011, 133, 9686-9688.
99. Endo, K.; Grubbs, R.H. Chelated Ruthenium Catalysts for ZSelective Olefin Metathesis. J. Am. Chem. Soc. 2011, 133, 8525-8527.
100. Teo, P.; Grubbs, R.H. Facile Synthesis of Effcient and Selective Ruthenium Olefin Metathesis Catalysts with Sulfonate and Phosphate Ligands. Organometallics 2010, 29, 6045-6050.
101. Rosen, E.L.; Sung, D.H.; Chen, Z.; Lynch, V.M.; Bielawski, C.W. Olefin Metathesis Catalysts Containing Acyclic Diaminocarbenes. Organometallics 2010, 29, 250-256.
102. Vougioukalakis, G.C.; Grubbs, R.H. Ruthenium-Based Olefin Metathesis Catalysts Coordinated with Unsymmetrical N-Heterocyclic Carbene Ligands: Synthesis, Structure, and Catalytic Activity. Chem. Eur. J. 2008, 14, 7545-7556.
103. France, M. B.; Paciello, R. A.; Grubbs, R. H. Initiation of ring-opening metathesis polymerization in protic media. Extension of [Ru(H2O)6]2+ catalyzed polymerizations to less-strained cyclic monomers. Macromolecules 1993, 26, 4739-4741.
104. Demonceau, A.; Stumpf, A.W.; Saive, E.; Noels, A.F. Novel Ruthenium-Based Catalyst Systems for the Ring-Opening Metathesis Polymerization of Low-Strain Cyclic Olefins. Macromolecules 1997, 30, 3127-3136.
105. Stumpf, A.W.; Saive, E.; Demonceau, A.; Noels, A.F. Ruthenium-Based Catalysts for the Ring Opening Metathesis Polymerisation of Low-Strain Cyclic Olefins and of Functionalised Derivatives of Norbornene and Cyclooctene. J. Chem. Soc., Chem. Commun. 1995, 1127-1128.
106. Monsaert, S.; Ledoux, N.; Drozdzak, R.; Verpoort, F. A highly controllable latent ruthenium Schiff base olefin metathesis catalyst: Catalyst activation and mechanistic studies. J. Polym. Sci. A, Polym. Chem. 2010, 48, 302-310.
107. Trimmer, M. S. Commercial Applications of Ruthenium Olefin Metathesis Catalysts in Polymer Synthesis. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 3, 407-418.
108. Kumar, A.; Srivastava, A.; Galaev, I.Y.; Mattiasson, B. Smart Polymers: Physical Forms and Bioengineering Applications. Prog. Polym. Sci. 2007, 32, 1205-1237.
109. Du, J.; O'Reilly, R.K. Advances and Challenges in Smart and Functional Polymer Vesicles. Soft Matter 2009, 5, 3544-3561.
110. Miyata, T. Preparation of Smart Soft Materials Using Molecular Complexes. Polym. J. 2010, 42, 277-289.
111. Gibson, S.E.; Swarmy, V.M. Microencapsulation of a Metathesis Catalyst. Adv. Synth. Catal. 2002, 344, 619-621.
112. Akiyama, R.; Kobayashi, S. Microencapsulated and Related Catalysts for Organic Chemistry and Organic Synthesis. Chem. Rev. 2009, 109, 594-642.
113. Lipshutz, B.H.; Ghorai, S. Organocatalysis in Water at Room Temperature with In-Flask Catalyst Recycling. Org. Lett. 2009, 11, 705-708.
114. Lipshutz, B.H.; Ghorai, S.; Leong, W.W.Y.; Taft, B.R. Manipulating Micellar Environments for Enhancing Transition Metal-Catalyzed Cross-Couplings in Water at Room Temperature. J. Org. Chem. 2011, 76, 5061-5073.
115. Coquerel, Y.; Rodriguez, J. Microwave-Assited Olefin Metathesis Eur. J. Org. Chem. 2008, 1125-1132.
116. Monsaert, S.; Lozano Vila, A.; Drozdzak, R.; Van der Voort, P.; Verpoort, F. Latent Olefin Metathesis Catalysts. Chem. Soc. Rev. 2009, 38, 3360-3372.
117. Szadkowska, A.; Grela, K. Initiation at a Snail's Pace: Design and Application of Latent Olefin Metathesis Catalysts Featuring Chelating Alkylidene Ligands. Curr. Org. Chem. 2008, 12, 1631-1647.
118. van der Schaaf, P.A., Kolly, R., Kirner, H.-J., Rime, F., Mühlebach, A., Hafner, A. Synthesis and reactivity of novel ruthenium carbene catalysts. Xray structures of [RuCl2(=CHSC6H5)(PiPr3)2] and [RuCl2(=CHCH2CH2-C,N-2-C5H4N)(PiPr3)]. J. Organomet. Chem. 2000, 606, 65-74.
119. Ung, T.; Hejl, A.; Grubbs, R.H.; Schrodi, Y. Latent Ruthenium Olefin Metathesis Catalysts That Contain an N-Heterocyclic Carbene Ligand. Organometallics 2004, 23, 5399-5401.
120. Hejl, A.; Day, M.W.; Grubbs, R.H. Latent Olefin Metathesis Catalysts Featuring Chelating Alkylidenes. Organometallics 2006, 25, 6149-6154.
121. Barbasiewicz, M.; Szadkowska, A.; Bujok, R.; Grela, K. Structure and Activity Peculiarities of Ruthenium Quinoline and Quinoxaline Complexes: Novel Metathesis Catalyst. Organometallics 2006, 23, 3599-3604.
122. Gstrein, X.; Burtscher, D.; Szadkowska, A.; Barbasiewicz, M.; Stelzer, F.; Grela, K.; Slugovc, C. Ruthenium Quinoline and Quinoxaline Complexes: Thermally Triggered Initiators for Ring Opening Metathesis Polymerization. J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 3494-3500.
123. Tsur, E.; Szadkowska, A.; Ben-Asuly, A.; Makal, A.; Goldberg, K.; Wozniak, K.; Grela, K.; Lemcoff, N.G. Studies on Electronic Effects in O-, N-and S-Chelated Ruthenium Olefin-Metathesis Catalysts. Chem. Eur. J. 2010, 16, 8726-8737.
124. Ben-Asuly, A.; Tzur, E.; Diesendruck, C.E.; Sigalov, M.; Goldberg, I.; Lemcoff, G.N. A Thermally Switchable Latent Ruthenium Olefin Metathesis Catalyst. Organometallics 2008, 27, 811-813.
125. Kost, T.; Sigalov, M.; Goldberg, I.; Ben-Asuly, A.; Lemcoff, G.N. Latent Sulfur Chelated Ruthenium Catalysts: Steric Acceleration Effects on Olefin Metathesis. J. Organomet. Chem. 2008, 693, 2200-2203.
126. Szadkowska, A.; Makal, A.; Wozniak, K.; Kadyrov, R.; Grela, K. Ruthenium Olefin Metathesis Initiators Bearing Chelating Sulfoxide Ligands. Organometallics 2009, 28, 2693-2700.
127. Lexer, C.; Burtscher, D.; Perner, B.; Tzur, E.; Lemcoff, N.G.; Slugovc, C. Olefin Metathesis Catalyst Bearing a Chelating Phosphine Ligand. J. Organomet. Chem. 2011, 696, 2466-2470.
128. Diesendruck, C.E.; Tzur, E.; Ben-Asuly, A.; Goldberg, I.; Straub, B.F.; Lemcoff, G.N. Photoactivation of Ruthenium Olefin Metathesis Initiators. Inorg. Chem. 2009, 48, 10819-10825.
129. Vidavsky, Y.; Anaby, A.; Lemcoff, N.G. Chelating Alkylidene Ligands as Pacifiers for Ruthenium Catalysed Olefin Metathesis. Dalton Trans. 2012, 41, 32-43.
130. Szadkowska, A.; Gstrein, X.; Burtscher, D.; Jarzembska, K.; Wozniak, K.; Grela, K.; Slugovc, C. Latent Thermo-Switchable Olefin Metathesis Initiators Bearing a Pyridyl-Functionalized Chelating Carbene: Influence of the Leaving Group's Rigidity on the Catalyst's Performance. Organometallics 2010, 29, 117-124.
131. Ben-Asuly, A.; Aharoni, A.; Diesendruck, C.E.; Vidavsky, Y.; Goldberg, I.; Straub, B.F.; Lemcoff, G.N. Photoactivation of Ruthenium Olefin Metathesis Initiators. Organometallics 2009, 28, 4652-4655.
132. Diesendruck, C.E.; Tzur, E.; Ben-Asuly, A.; Goldberg, I.; Straub, B.F.; Lemcoff, G.N. A Latent S-Chelated Ruthenium Benzylidene Initiator for Ring-Opening Metathesis Polymerization. Polym. Sci. Part A: Polym. Chem. 2009, 47, 4209-4213.
133. Barbasiewicz, M.; Blocki, K.; Malinska, M.; Pawlowski, R. Intriguing Substituent Effect in Modified Hoveyda-Grubbs Metathesis Catalysts Incorporating a Chelating Iodo-Benzylidene Ligand. Dalton Trans. 2013, 42, 355-358.
134. Barbasiewicz, M.; Michalak, M.; Grela, K. A New Family of Halogen-Chelated Hoveyda-Grubbs-Type Metathesis Catalysts. Chem. Eur. J. 2012, 45, 3264-3268.
135. Louie, J.; Grubbs, R.H. Metathesis of Electron-Rich Olefins: Structure and Reactivity of Electron-Rich Carbene Complexes. Organometallics 2002, 21, 2153-2164.
136. Opstal, T.; Verpoort, F. Easily Accessible and Robust Olefin-Metathesis Catalysts Based on Ruthenium Vinylidene Complexes. J. Mol. Catal. A: Chem. 2003, 200, 49-61.
137. Schanz, H.-J.; Jafarpour, L.; Stevens, E.D.; Nolan, S.P. Coordinatively Unsaturated 16-Electron Ruthenium Allenylidene Complexes: Synthetic, Structural, and Catalytic Studies. Organometallics 1999, 18, 5187-5190.
138. Hudson, D.M.; Valente, E.J.; Schachner, J.; Limbach, M.; Müller, K.B.; Schanz, H.-J. A Ru-vinylvinylidene Complex: Straightforward Synthesis of a Latent Olefin Metathesis Catalyst. ChemCatChem 2011, 3, 297-301.
139. Ledoux, N.; Allaert, B.; Schaubroeck, D.; Monsaert, S.; Drozdzak, R.; van der Voort, P.; Verpoort, F. In situ Generation of Highly Active Olefin Metathesis Initiators. J. Organomet. Chem. 2006, 691, 5482-5486.
140. Allaert, B.; Dieltens, N.; Ledoux, N.; Vercaemst, C.; van der Voort, P.; Stevens, C.V.; Linden, A.; Verpoort, F. Synthesis and Activity for ROMP of Bidentate Schiff Base Substituted Second Generation Grubbs Catalysts. J. Mol. Catal. A: Chem. 2006, 260, 221-226.
141. DeClerq, B.; Verpoort, F. Activity of a New Class of Ruthenium Based Ring-Closing Metathesis and Ring-Opening Metathesis Polymerization Catalysts Coordinated with a 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff Base Ligand. Tetrahedron Lett. 2002, 43, 9101-9104.
142. Occhipinti, G.; Bjørsvik, H.-R.; Törnroos, K.W.; Jensen, V.R. Ruthenium Alkylidene Complexes of Chelating Amine Ligands. Organometallics 2007, 26, 5803-5814.
143. Denk, K.; Fridgen, J.; Herrmann, W.A. N-Heterocyclic Carbenes, Part 33. Combining Stable NHC and Chelating Pyridinyl-Alcoholato Ligands: A Ruthenium Catalyst for Applications at Elevated Temperatures. Adv. Synth. Catal. 2002, 34, 666-670.
144. Cabrera, J.; Padilla, R.; Bru, M.; Lindner, R.; Kageyama, T.; Wilckens, K.; Balof, S.L.; Schanz, H.-J.; Dehn, R.; Teles, J.H.; Deuerlein, S.; Müller, K.; Rominger, F.; Limbach, M. Linker Free, Silica Bound Olefin Metathesis Catalysts: Applications in Heterogeneous Catalysis. Chem. Eur. J. 2012, 18, 14717-14724.
145. Vorfalt, T.; Leuthäusser, S.; Plenio, H. An [(NHC)(NHCEWG) RuCl2(CHPh)] Complex for the Efficient Formation of Sterically Hindered Olefins by Ring-Closing Metathesis. Angew. Chem. Int. Ed. 2009, 48, 5191-5192.
146. Sashuk, V.; Peeck, L. H.; Plenio, H. [(NHC)(NHCewg) RuCl2(CHPh)] Complexes with Modified NHCewg Ligands for Efficient Ring-Closing Metathesis Leading to Tetrasubstituted Olefins. Chem. Eur. J. 2010, 16, 3983-3993.
147. Peeck, L.H.; Plenio, H. Synthesis and RCM Activity of [(NHC)(NHCewg)RuCl2(3-phenylindenylid-1-ene)] Complexes. Organometallics 2010, 29, 2761-2766.
148. Urbina-Blanco C.A., Leitgelb A., Slugovc, C.; Bantreil, X.; Clavier, H.; Slawin, A.M.Z.; Nolan, S.P. Olefin Metathesis Featuring Ruthenium Indenylidene Complexes with a Sterically Demanding NHC Ligand. Chem. Eur. J. 2011, 17, 5045-5053.
149. Bantreil, X.; Randall, R.A.M.; Slawin, A.M.Z.; Nolan, S.P. Ruthenium Complexes Bearing Two N-Heterocyclic Carbene Ligands in Low Catalyst Loading Olefin Metathesis Reactions. Organometallics 2010, 29, 3007-3011.
150. Thomas, R.M.; Fedorov, A.; Keitz, B.K.; Grubbs, R.H. Thermally Stable, Latent Olefin Metathesis Catalysts. Organometallics 2011, 30, 6713-6717.
151. Bantreil, X.; Poater, A.; Urbina-Blanco, C.A.; Bidal, Y.D.; Falivene, L.; Randall, R.A.M.; Cavallo, L.; Slawin, A.M.Z.; Cazin, C.S.J. Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes. Organometallics 2012, 31, 7415-7426.
152. Bantreil, X.; Schmid, T.E.; Randall, R.A.M.; Slawin, A.M.Z.; Cazin, C.S.J. Mixed N-Heterocyclic Carbene/Phosphite Ruthenium Complexes: Towards a New Generation of Olefin Metathesis Catalysts. Chem. Commun. 2010, 46, 7115-7117.
153. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Stereoelectronic Effects Characterizing Nucleophilic Carbene Ligands Bound to the Cp*RuCl (Cp* = σ5-C5Me5) Moiety: A Structural and Thermochemical Investigation. Organometallics 1999, 18, 5375-5380.
154. P'Pool, S.J.; Schanz, H.-J. Reversible Inhibition/Activation of Olefin Metathesis: A Kinetic Investigation of ROMP and RCM Reactions with Grubbs' Catalyst. J. Am. Chem. Soc. 2007, 129, 14200-14212.
155. Dunbar, M.A.; Balof, S.L.; LaBeaud, L.J.; Yu, B.; Lowe, A.B.; Valente, E.J.; Schanz, H.-J. Improved Molecular Weight Control in Ring Opening Metathesis Polymerization Reactions with Ru-Based Olefin Metathesis Catalysts Using N-Donors and Acid: A Kinetic and Mechanistic Investigation. Chem. Eur. J. 2009, 15, 12435-12446.
156. Hahn, F.E.; Paas, M.; Fröhlich, R. Synthesis, Characterization, and Catalytic Activity of a Ruthenium Carbene Complex Coordinated with Bidentate 2-Pyridine-Carboxylato Ligands. J. Organomet. Chem. 2005, 690, 5816-5821.
157. Samec, J.S.M.; Keitz, B.K.; Grubbs, R.H. Latent Ruthenium Olefin Metathesis Catalysts Featuring a Phosphine or an N-Heterocyclic Carbene Ligand. J. Organomet. Chem. 2010, 695, 1831-1837.
158. Bienik, M.; Bujok, R.; Cabaj, M.; Lugan, N.; Lavigne, G.; Arlt, D.; Grela, K. Advanced Fine-Tuning of Grubbs/Hoveyda Olefin Metathesis Catalysts: A Further Step toward an Optimum Balance between Antinomic Properties. J. Am. Chem. Soc. 2006, 128, 13652-13653.
159. Gawin, R.; Makal, A.; Wozniak, K.; Mauduit, M.; Grela, K. A Dormant Ruthenium Catalyst Bearing a Chelating Carboxylate Ligand: In Situ Activation and Application in Metathesis Reactions. Angew. Chem. Int. Ed. 2007, 46, 7206-7209.
160. Pietraszuk, C.; Rogalski, S.; Powala, B.; Mietkiewski, M.; Kubicki, M.; Spolnik, G.; Danikiewicz, W.; Wozniak, K.; Pazio, A.; Szadkowska, A.; Kozlowska, A., Grela, K. Ruthenium-Amido Complexes: Synthesis, Structure, and Catalytic Activity in Olefin Metathesis. Chem. Eur. J. 2012, 18, 6465-6469.
161. Keitz, B.K.; Grubbs, R. H. A Tandem Approach to Photoactivated Olefin Metathesis: Combining a Photoacid Generator with an Acid Activated Catalyst. J. Am. Chem. Soc. 2009, 131, 2038-2039.
162. Khalimon, A.Y.; Leitao, E.M.; Piers, W.E. Photogeneration of a Phosphonium Alkylidene Olefin Metathesis Catalyst. Organometallics 2012, 31, 5634-5637.
163. Romero, P.E.; Piers, W.E.; McDonald, R. Rapidly Initiating Ruthenium Olefin-Metathesis Catalysts. Angew. Chem. Int. Ed. 2004, 43, 6161-6165.
164. Dubberly, S.R.; Romero, P.E.; Piers, W.E.; McDonald, R.; Parvez, M. Synthesis, characterization and olefin metathesis studies of a family of ruthenium phosphonium alkylidene complexes. Inorg. Chim. Acta 2006, 359, 2658-2664.
165. Gulajski, L.; Michrowska, A.; Bujok, R.; Grela, K. New Tunable Catalysts for Olefin Metathesis: Controlling the Initiation through Electronic Factors. J. Mol. Catal. A: Chem. 2006, 254, 118-123.
166. Catalyst 45 was originally synthesized in Grubbs group, see ref. [15]
167. Roberts, A.N.; Cochran, A.C.; Rankin, D.A.; Lowe, A.B.; Schanz, H.-J. Benzylidene-Functionalized Ruthenium-Based Olefin Metathesis Catalysts for ROMP Organic and Protic Media. Organometallics 2007, 26, 6515-6518.
168. Dunbar, M.A.; Balof, S.L.; Roberts, A.N.; Valente, E.J.; Schanz, H.-J. pHResponsive Ruthenium-Based Olefin Metathesis Catalysts: Controlled Ring Opening Metathesis Polymerization in Alcoholic and Aqueous Media upon Acid Addition. Organometallics 2011, 30, 199-203.
169. Balof, S.L.; P'Pool, S.J.; Berger, N.J.; Valente, E.J.; Schiller, A.M.; Schanz, H.-J. Olefin Metathesis Catalysts Bearing a pH-Responsive NHC Ligand: A Feasible Approach to Catalyst Separation from RCM Products. Dalton Trans. 2008, 5791-5799.
170. Balof, S.L.; Yu, B.; Lowe, A.B.; Ling, Y.; Zhang, Y.; Schanz, H.-J. Ru-Based Olefin Metathesis Catalysts Bearing pH-Responsive N-Heterocyclic Carbene (NHC) Ligands: Activity Control via Degree of Protonation. Eur. J. Inorg. Chem. 2009, 1717-1722.
171. Leuthäusser, S.; Schmidts, V.; Thiele, C.M.; Plenio, H. π-Face Donor Properties of N-Heterocyclic Carbenes in Grubbs II Complexes. Chem. Eur. J. 2008, 14, 5465-5481.
172. Peeck, L.H.; Leuthäusser, S.; Plenio, H. Switched Stereocontrol in Grubbs-Hoveyda Complex Catalyzed ROMP Utilizing Proton-Switched NHC Ligands. Organometallics 2010, 29,4339-4345.
173. Wang, D.; Wurst, K.; Knolle, W.; Decker, U.; Prager, L.; Naumov, S.; Buchmeiser, M.R. Cationic RuII Complexes with N-Heterocyclic Carbene Ligands for UV-Induced Ring-Opening Metathesis Polymerization. Angew. Chem. Int. Ed. 2008, 47, 3267-3270.
174. Fürstner, A.; Ackermann, L. A most user-friendly protocol for ring closing metathesis reactions. Chem. Commun. 1999, 95-96.
175. Hafner, A.; Mühlbach, A.; van der Schaaf, P.A. One-Component Catalysts for Thermal and Photoinduced Ring Opening Metathesis Polymerization. Angew. Chem. Int. Ed. 1997, 36, 2121-2124.
176. Buchmeiser, M.R.; Wang, D.; Zhang, Y.; Naumov, S.; Wurst, K. Novel Ruthenium(II) N-Heterocyclic Carbene Complexes as Catalyst Precursors for the Ring-Opening Metathesis Polymerization (ROMP) of Enantiomerically Pure Monomers: X-ray Structures, Reactivity, and Quantum Chemical Considerations. Eur. J. Inorg. Chem. 2007, 3988-4000.
177. Ginzburg, Y.; Anaby, A.; Vidavski, Y.; Diesendruck, C.E.; Ben-Asuly, A.; Goldberg, I.; Lemcoff, N.G. Widening the Latency Gap in Chelated Ruthenium Olefin Metathesis Catalysts. Organometallics 2011, 30, 3430-3437.
178. Liu, G.; Wang, J. Recycling a Homogeneous Catalyst through a Light-Controlled Phase Tag. Angew. Chem. Int. ed. 2010, 49, 4425-4429.
179. Süßner, M.; Plenio, H. Redox-Switchable Phase Tags for Recycling of Homogeneous Catalysts. Angew. Chem. Int. ed. 2005, 44, 6885-6888.
180. Tuba, R.; da Costa, R.C.; Bazzi, H.S.; Gladysz, J.A. Phase Transfer Activation of Fluorous Analogs of Grubbs' Second-Generation Catalyst: Ring-Opening Metathesis Polymerization. ACS Catal. 2012, 2, 155-162.
181. Piermattei, A.; Karthikeyan, S.; Sijbesma, R.P. Activating catalysts with mechanical force. Nature Chem. 2009, 1, 133-137.
182. Groote, R.; Jakobs, R.T.; Sijbesma, R.P. Performance of Mechanochemically Activated Catalysts is Enhanced by Suppression of the Thermal Effects of Ultrasound. ACS Macro Lett. 2012, 1, 1012-1015.
183. Claverie, J.P.; Viala, S.; Maurel, V.; Novat, C. Ring-Opening Metathesis Polymerization in Emulsion. Macromolecules 2001, 34, 382-388.
184. Quemener, D.; Heroguez, V.; Gnanou, Y. Latex Particles by Miniemulsion Ring-Opening Metathesis Polymerization. Macromolecules 2005, 38, 7977-7982.
185. Quemener, D.; Chemtob, A.; Heroguez, V.; Gnanou, Y. Synthesis of Latex Particles by Ring-Opening Metathesis Polymerization. Polymer 2005, 46, 1067-1075.
186. Caruso, M.M.; Davies, D.A.; Shen, Q.; Odom, S.A.; Sottos, N.R.; White, S.R.; Moore, J.S. Mechanically-Induced Chemical Changes in Polymeric Materials. Chem. Rev. 2009, 109, 5755-5798.