Synthesis and catalytic applications of iron pincer complexes

Comments on Inorganic Chemistry

Volumn 32, Issue 2, 2011, Pages 88-112

  Bhattacharya, Papri ^a   Guan, Hairong ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

C H bond activation; Cross coupling reactions; First row transition metals; Homogeneous catalysis; Hydrogenation; Hydrosilylation; Iron; Pincer complexes

Indexed keywords

EID: 84855743339     PISSN: 02603594     EISSN: 15489574     Source Type: Journal    
DOI: 10.1080/02603594.2011.618855     Document Type: Review

References (109)

1. Kauffman, G. B. Alfred Werner: Founder of Coordination Chemistry; Springer-Verlag: New York, 1966.
2. Morales-Morales, D.; Jensen, C. M. The Chemistry of Pincer Compounds; Elsevier: Amsterdam, 2007.
3. Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Diaminoarylnickel(II) 'Pincer' Complexes: Mechanistic Considerations in the Kharasch Addition Reaction, Controlled Polymerization, and Dendrimeric Transition Metal Catalysts. Acc. Chem. Res. 1998, 31, 423-431.
4. Albrecht, M.; van Koten, G. Platinum Group Organometallics Based on 'Pincer' Complexes: Sensors, Switches, and Catalysts. Angew. Chem. Int. Ed. 2001, 40, 3750-3781.
5. van der Boom, M. E.; Milstein, D. Cyclometalated Phosphine-Based Pincer Complexes: Mechanistic Insight in Catalysis, Coordination, and Bond Activation. Chem. Rev. 2003, 103, 1759-1792.
6. Singleton, J. T. The Uses of Pincer Complexes in Organic Synthesis. Tetrahedron 2003, 59, 1837-1857.
7. Morales-Morales, D. Pincer Complexes. Applications in Catalysis. Rev. Soc. Qui{dotless}́m. Méx. 2004, 48, 338-346.
8. Peris, E.; Crabtree, R. H. Recent Homogeneous Catalytic Applications of Chelate and Pincer N-Heterocyclic Carbenes. Coord. Chem. Rev. 2004, 248, 2239-2246.
9. Liang, L.-C. Metal Complexes of Chelating Diarylamido Phosphine Ligands. Coord. Chem. Rev. 2006, 250, 1152-1177.
10. Nishiyama, H. Synthesis and Use of Bisoxazolinyl-Phenyl Pincers. Chem. Soc. Rev. 2007, 36, 1133-1141.
11. Pugh, D.; Danopoulos, A. A. Metal Complexes with 'Pincer'-Type Ligands Incorporating N-Heterocyclic Carbene Functionalities. Coord. Chem. Rev. 2007, 251, 610-641.
12. Morales-Morales, D. Recent Applications of Phosphinite POCOP Pincer Complexes towards Organic Transformations. Mini-Rev. Org. Chem. 2008, 5, 141-152.
13. Leis, W.; Mayer, H. A.; Kaska, W. C. Cycloheptatrienyl, Alkyl and Aryl PCP-Pincer Complexes: Ligand Backbone Effects and Metal Reactivity. Coord. Chem. Rev. 2008, 252, 1787-1797.
14. Benito-Garagorri, D.; Kirchner, K. Modularly Designed Transition Metal PNP and PCP Pincer Complexes based on Aminophosphines: Synthesis and Catalytic Applications. Acc. Chem. Res. 2008, 41, 201-213.
15. Nishiyama, H.; Ito, J. Bis(oxzaolinyl)phenyl Transition-Metal Complexes: Asymmetric Catalysis and Some Reactions of the Metals. Chem. Commun. 2010, 46, 203-212.
16. Choi, J.; MacArthur, A. H. R.; Brookhart, M.; Goldman, A. S. Dehydro-genation and Related Reactions Catalyzed by Iridium Pincer Complexes. Chem. Rev. 2011, 111, 1761-1779.
17. Selander, N.; Szabó, K. J. Catalysis by Palladium Pincer Complexes. Chem. Rev. 2011, 111, 2048-2076.
18. Bullock, R. M. Catalysis without Precious Metals; Wiley-VCH: Weinheim, 2010.
19. Kulkarni, A. A.; Daugulis, O. Direct Conversion of Carbon-Hydrogen into Carbon-Carbon Bonds by First-Row Transition-Metal Catalysis. Synthesis 2009, 4087-4109.
20. Chakraborty, S.; Guan, H. First-Row Transition Metal Catalyzed Reduction of Carbonyl Functionalities: A Mechanistic Perspective. Dalton Trans. 2010, 39, 7427-7436.
21. Plietker, B. Iron Catalysis in Organic Chemistry; Wiley-VCH: Weinheim, 2008.
22. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Iron-Catalyzed Reactions in Organic Synthesis. Chem. Rev. 2004, 104, 6217-6254.
23. Enthaler, S.; Junge, K.; Beller, M. Sustainable Metal Catalysis with Iron: From Rust to a Rising Star? Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
24. Gaillard, S.; Renaud, J.-L. Iron-Catalyzed Hydrogenation, Hydride Transfer, and Hydrosilylation: An Alternative to Precious-Metal Complexes? ChemSusChem 2008, 1, 505-509.
25. Bauer, E. B. Recent Advances in Iron Catalysis in Organic Synthesis. Curr. Org. Chem. 2008, 12, 1341-1369.
26. Morris, R. H. Asymmetric Hydrogenation, Transfer Hydrogenation and Hydrosilylation of Ketones Catalyzed by Iron Complexes. Chem. Soc. Rev. 2009, 38, 2282-2291.
27. Liu, L.-X. Recent Uses of Iron Catalysts in Organic Reactions. Curr. Org. Chem. 2010, 14, 1099-1126.
28. Zhang, M.; Zhang, A. Iron-Catalyzed Hydrosilylation Reactions. Appl. Organomet. Chem. 2010, 24, 751-757.
29. Junge, K.; Schroder, K.; Beller, M. Homogeneous Catalysis Using Iron Complexes: Recent Developments in Selective Reductions. Chem. Commun. 2011, 47, 4849-4859.
30. Nakazawa, H.; Itazaki, M. Fe H Complexes in Catalysis. Top. Organomet. Chem. 2011, 33, 27-81.
31. Mikhailine, A.; Lough, A. J.; Morris, R. H. Efficient Asymmetric Transfer Hydrogenation of Ketones Catalyzed by an Iron Complex Containing a P-N-N-P Tetradentate Ligand Formed by Template Synthesis. J. Am. Chem. Soc. 2009, 131, 1394-1395.
32. Meyer, N.; Lough, A. J.; Morris, R. H. Iron(II) Complexes for the Efficient Catalytic Asymmetric Transfer Hydrogenation of Ketones. Chem. Eur. J. 2009, 15, 5605-5610.
33. Lagaditis, P. O.; Lough, A. J.; Morris, R. H. Iron Complexes for the Catalytic Transfer Hydrogenation of Acetophenone: Steric and Electronic Effects Imposed by Alkyl Substituents at Phosphorus. Inorg. Chem. 2010, 49, 10057-10066.
34. Mikhailine, A. A.; Morris, R. H. Effect of the Structure of the Diamine Backbone of P-N-N-P ligands in Iron(II) Complexes on Catalytic Activity in the Transfer Hydrogenation of Acetophenone. Inorg. Chem. 2010, 49, 11039-11044.
35. Lagaditis, P. O.; Lough, A. J.; Morris, R. H. Low-Valent Ene-Amido Iron Complexes for the Asymmetric Transfer Hydrogenation of Acetophenone without Base. J. Am. Chem. Soc. 2011, 133, 9662-9665.
36. Moulton, C. J.; Shaw, B. L. Transition Metal-Carbon Bonds. Part XLII. Complexes of Nickel, Palladium, Platinum, Rhodium and Iridium with the Tridentate Ligand 2,6-Bis[(di-t-butylphosphino)methyl]phenyl. J. Chem. Soc., Dalton Trans. 1976, 1020-1024.
37. Bianchini, C.; Giambastiani, G.; Guerrero Rios, I.; Mantovani, G.; Meli, A.; Segarra, A. M. Ethylene Oigomerization, Homopolymerization and Copolymerization by Iron and Cobalt Catalysts with 2,6-(Bis-organylimino)pyridyl Ligands. Coord. Chem. Rev. 2006, 250, 1391-1418.
38. Gibson, V. C.; Redshaw, C.; Solan, G. A. Bis(imino)pyridines: Surprisingly Reactive Ligands and a Gateway to New Families of Catalysts. Chem. Rev. 2007, 107, 1745-1776.
39. Small, B. L.; Brookhart, M.; Bennett, A. M. A. Highly Active Iron and Cobalt Catalysts for the Polymerization of Ethylene. J. Am. Chem. Soc. 1998, 120, 4049-4050.
40. Small, B. L.; Brookhart, M. Iron-Based Catalysts with Exceptionally High Activities and Selectivities for Oligomerization of Ethylene to Linear a-Olefins. J. Am. Chem. Soc. 1998, 120, 7143-7144.
41. Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Novel Olefin Polymerization Catalysts Based on Iron and Cobalt. Chem. Commun. 1998, 849-850.
42. Britovsek, G. J. P.; Bruce, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J.; Redshaw, C.; Solan, G. A.; Stromberg, S.; White, A. J. P.; Williams, D. J. Iron and Cobalt Ethylene Polymerization Catalysts Bearing 2,6-Bis(Imino)Pyridyl Ligands: Synthesis, Structures, and Polymerization Studies. J. Am. Chem. Soc. 1999, 121, 8728-8740.
43. Bart, S. C.; Lobkovsky, E.; Chirik, P. J. Preparation and Molecular and Electronic Structures of Iron(0) Dinitrogen and Silane Complexes and Their Application to Catalytic Hydrogenation and Hydrosilation. J. Am. Chem. Soc. 2004, 126, 13794-13807.
44. Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik, P. J. Synthesis and Hydrogenation of Bis(imino)pyridine Iron Imides. J. Am. Chem. Soc. 2006, 128, 5302-5303.
45. Trovitch, R. J.; Lobkovsky, E.; Bill, E.; Chirik, P. J. Functional Group Tolerance and Substrate Scope in Bis(imino)pyridine Iron Catalyzed Alkene Hydrogenation. Organometallics 2008, 27, 1470-1478.
46. Russell, S. K.; Darmon, J. M.; Lobkovsky, E.; Chirik, P. J. Synthesis of Aryl-Substituted Bis(imino)pyridine Iron Dinitrogen Complexes. Inorg. Chem. 2010, 49, 2782-2792.
47. Russell, S. K.; Milsmann, C.; Lobkovsky, E.; Weyhermuller, T.; Chirik, P. J. Synthesis, Electronic Structure, and Catalytic Activity of Reduced Bis(aldimino)pyridine Iron Compounds: Experimental Evidence for Ligand Participation. Inorg. Chem. 2011, 50, 3159-3169.
48. Tondreau, A. M.; Lobkovsky, E.; Chirik, P. J. Bis(imino)pyridine Iron Complexes for Aldehyde and Ketone Hydrosilylation. Org. Lett. 2008, 10, 2789-2792.
49. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. Iron-Catalyzed [2p {thorn} 2p] Cycloaddition of a,x-Dienes: The Importance of Redox-Active Supporting Ligands. J. Am. Chem. Soc. 2006, 128, 13340-13341.
50. Russell, S. K.; Lobkovsky, E.; Chirik, P. J. Iron-Catalyzed Intermolecular [2p {thorn} 2p] Cycloaddition. J. Am. Chem. Soc. 2011, 133, 8858-8861.
51. D'Souza, B. R.; Lane, T. K.; Louie, J. Iron-Catalyzed Cycloaddition of Alkynenitriles and Alkynes. Org. Lett. 2011, 13, 2936-2939.
52. Sylvester, K. T.; Chirik, P. J. Iron-Catalyzed, Hydrogen-Mediated Reductive Cyclization of 1,6-Enynes and Diynes: Evidence for Bis(imino)pyridine Ligand Participation. J. Am. Chem. Soc. 2009, 131, 8772-8774.
53. Tondreau, A. M.; Darmon, J. M.; Wile, B. M.; Floyd, S. K.; Lobkovsky, E.; Chirik, P. J. Enantiopure Pyridine Bis(oxazoline) 'Pybox' and Bis(oxazoline) 'Box' Iron Dialkyl Complexes: Comparison to Bis(imino)pyridine Compounds and Application to Catalytic Hydrosilylation of Ketones. Organometallics 2009, 28, 3928-3940.
54. 00-terpyridine Ligand. Eur. J. Inorg. Chem. 2007, 2111-2120.
55. 0, N-Bis(methyl-L-prolinate)-Substituted Pyridine Ligand. Inorg. Chem. 2006, 45, 4214-4227.
56. Xiao, L.; Gao, R.; Zhang, M.; Li, Y.; Cao, X.; Sun, W.-H. 2-(1H-2-Benzimidazolyl)-6-(1-(Arylimino)Ethyl)pyridyl Iron(II) and Cobalt(II) Dichlorides: Syntheses, Characterizations, and Catalytic Behaviors toward Ethylene Reactivity. Organometallics 2009, 28, 2225-2233.
57. Liu, Y.; Yan, X.; Yang, N.; Xi, C. Highly Regioselective Cyclotrimerization of Terminal Alkynes Catalyzed by Fe(II) Complexes Bearing 2-(Benzimidazolyl)-6-(1-(Arylimino)Ethyl)pyridines. Catal. Commun. 2011, 12, 489-492.
58. Albrecht, M. Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends. Chem. Rev. 2010, 110, 576-623.
59. Creaser, C. S.; Kaska, W. C. Complexes of 1,3-Bis(dimethylphosphino-methyl)-benzene with Nickel(II), Palladium(II) and Iron(II) Halides. Inorg. Chim. Acta 1978, 30, L325-L326.
60. 3 Carbon-Hydrogen Bonds by Cobalt and Iron Complexes and Subsequent C-C Bond Formation. Organometallics 2009, 28, 6090-6095.
61. Chakraborty, S.; Krause, J. A.; Guan, H. Hydrosilylation of Aldehydes and Ketones Catalyzed by Nickel PCP-Pincer Hydride Complexes. Organometallics 2009, 28, 582-586.
62. Chakraborty, S.; Zhang, J.; Krause, J. A.; Guan, H. An Efficient Nickel Catalyst for the Reduction of Carbon Dioxide with a Borane. J. Am. Chem. Soc. 2010, 132, 8872-8873.
63. Zhang, J.; Medley, C. M.; Krause, J. A.; Guan, H. Mechanistic Insights into C S Cross-Coupling Reactions Catalyzed by Nickel Bis(phosphinite) Pincer Complexes. Organometallics 2010, 29, 6393-6401.
64. Huang, F.; Zhang, C.; Jiang, J.; Wang, Z.-X.; Guan, H. How Does the Nickel Pincer Complex Catalyze the Conversion of CO2 to a Methanol Derivative? A Computational Mechanistic Study. Inorg. Chem. 2011, 50, 3816-3825.
65. Chakraborty, S.; Patel, Y. J.; Krause, J. A.; Guan, H. Catalytic Properties of Nickel Bis(phosphinite) Pincer Complexes in the Reduction of CO2 to Methanol Derivatives. Polyhedron 2011, in press.
66. Bhattacharya, P.; Krause, J. A.; Guan, H. Iron Hydride Complexes Bearing Phosphinite-Based Pincer Ligands: Synthesis, Reactivity, and Catalytic Application in Hydrosilylation Reactions. Organometallics 2011, 30, 4720-4729.
67. Hosokawa, S.; Ito, J.; Nishiyama, H. A Chiral Iron Complex Containing a Bis(oxazolinyl)phenyl Ligand: Preparation and Asymmetric Hydrosilylation of Ketones. Organometallics 2010, 29, 5773-5775.
68. de Koster, A.; Kanters, J. A.; Spek, A. L.; van der Zeijden, A. A. H.; van Koten, G.; Vrieze, K. Structure of f2,6-Bis[(dimethylamino)methyl]phenylg dichloroiron (III), [Fe(C12H19N2)Cl2]. Acta Cryst. 1985, C41, 893-895.
69. Fryzuk, M. D.; Leznoff, D. B.; Ma, E. S. F.; Rettig, S. J.; Young, Jr., V. G. Synthesis, Structure, and Reactivity of Paramagnetic Iron(II) and Iron(III) Amidodiphosphine Complexes. Organometallics 1998, 17, 2313-2323.
70. tBu2PCH2SiMe2)2N]Fe, -Co, and -Ni. Inorg. Chem. 2008, 47, 407-409.
71. Adhikari, D.; Basuli, F.; Fan, H.; Huffman, J. C.; Pink, M.; Mindiola, D. J. P=N Bond Formation via Incomplete N-Atom Transfer from a Ferrous Amide Precursor. Inorg. Chem. 2008, 47, 4439-4441.
72. Kruck, M.; Sauer, D. C.; Enders, M.; Wadepohl, H.; Gade, L. H. Bis(2-pyridylimino)isoindolato Iron(II) and Cobalt(II) Complexes: Structural Chemistry and Paramagnetic NMR Spectroscopy. Dalton Trans. 2011, 40, 10406-10415.
73. Boudier, A.; Breuil, P.-A. R.; Magna, L.; Rangheard, C.; Ponthus, J.; Olivier-Bourbigou, H.; Braunstein, P. Novel Catalytic System for Ethylene Oligomerization: An Iron(III) Complex with an Anionic N, N, N Ligand. Organometallics 2011, 30, 2640-2642.
74. Steenwinkel, P.; Jastrzebski, J. T. B. H; Deelman, B.-J.; Grove, D. M.; Kooijman, H.; Veldman, N.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Hypercoordinate Aryltrialkylsilanes and -stannanes and their Use in the Synthesis of Homodinuclear Organometallic Complexes with a 1,4-Phenylene Bridge. Organometallics 1997, 16, 5486-5498.
75. Weintrob, E. C.; Tofan, D.; Bercaw, J. E. Synthesis and Characterization of Iron Derivatives Having a Pyridine-Linked Bis(anilide) Pincer Ligand. Inorg. Chem. 2009, 48, 3808-3813.
76. Contel, M.; Stol, M.; Casado, M. A.; van Klink, G. P. M.; Ellis, D. D.; Spek, A. L.; van Koten, G. A Bis(ortho-amine)aryl-Gold(I) Compound as an Efficient, Nontoxic, Arylating Reagent. Organometallics 2002, 21, 4556-4559.
77. Dahlhoff, W. V.; Nelson, S. M. Studies on the Magnetic Cross-over in Five-Coordinate Complexes of Iron(II), Cobalt (II), and Nickel(II). Part II. J. Chem. Soc. A 1971, 2184-2190.
78. Zhang, J.; Gandelman, M.; Herrman, D.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Iron(II) Complexes Based on Electron-Rich, Bulky PNN and PNP-Type Ligands. Inorg. Chim. Acta 2006, 359, 1955-1960.
79. Pelczar, E. M.; Emge, T. J.; Krogh-Jespersen, K.; Goldman, A. S. Unusual Structural and Spectroscopic Features of Some PNP-Pincer Complexes of Iron. Organometallics 2008, 27, 5759-5767.
80. Benito-Garagorri, D.; Becker, E.; Wiedermann, J.; Lackner, W.; Pollak, M.; Mereiter, K.; Kisala, J.; Kirchner, K. Achiral and Chiral Transition Metal Complexes with Modularly Designed Tridentate PNP Pincer-Type Ligands Based on N-Heterocyclic Diamines. Organometallics 2006, 25, 1900-1913.
81. Nakajima, Y.; Nakao, Y.; Sakaki, S.; Tamada, Y.; Ono, T.; Ozawa, F. Electronic Structure of Four-Coordinate Iron(I) Complex Supported by a Bis(phosphaethenyl)pyridine Ligand. J. Am. Chem. Soc. 2010, 132, 9934-9936.
82. Danopoulos, A. A.; Tsoureas, N.; Wright, J. A.; Light, M. E. N-Hetero-cyclic Pincer Dicarbene Complexes of Iron(II): C-2 and C-5 Metalated Carbenes on the Same Metal Center. Organometallics 2004, 23, 166-168.
83. 0: Experimental and Computational Comparison of the Phosphine and NHC Donors. Chem. Eur. J. 2009, 15, 5491-5502.
84. Giannoccaro, P.; Vasapollo, G.; Nobile, C. F.; Sacco, A. 2,6-Bis(diphenyl-phosphinomethyl)pyridine Complexes of Nickel(II), Cobalt(II), Iron (II). Inorg. Chem. Acta 1982, 61, 69-75.
85. {thorn} Moiety. Inorg. Chem. 2008, 47, 5129-5135.
86. Walstrom, A. N.; Fullmer, B. C.; Fan, H.; Pink, M.; Buschhorn, D. T.; Caulton, K. G. Influence of the Metal Orbital Occupancy and Principal Quantum Number on Organoazide (RN3) Conversion to Transition-Metal Imide Complexes. Inorg. Chem. 2008, 47, 9002-9009.
87. Bouwkamp, M. W.; Lobkovsky, E.; Chirik, P. J. Bis(imino)pyridine Ligand Deprotonation Promoted by a Transient Iron Amide. Inorg. Chem. 2006, 45, 2-4.
88. Danopoulos, A. A.; Wright, J. A.; Motherwell, W. B. Molecular N2 Complexes of Iron Stabilised by N-Heterocyclic 'Pincer' Dicarbene Ligands. Chem. Commun. 2005, 784-786.
89. Pugh, D.; Wells, N. J.; Evans, D. J.; Danopoulos, A. A. Reactions of 'Pincer' Pyridine Dicarbene Complexes of Fe(0) with Silanes. Dalton Trans. 2009, 7189-7195.
90. Benito-Garagorri, D.; Puchberger, M.; Mereiter, K.; Kirchner, K. Stereospecific and Reversible CO Binding at Iron Pincer Complexes. Angew. Chem. Int. Ed. 2008, 47, 9142-9145.
91. Benito-Garagorri, D.; Alves, L. G.; Puchberger, M.; Mereiter, K.; Veiros, L. F.; Calhorda, M. J.; Carvalho, M. D.; Ferreira, L. P.; Godinho, M.; Kirchner, K. Striking Differences between the Solution and Solid-State Reactivity of Iron PNP Pincer Complexes with Carbon Monoxide. Organometallics 2009, 28, 6902-6914.
92. Benito-Garagorri, D.; Alves, L. G.; Veiros, L. F.; Standfest-Hauser, C. M.; Tanaka, S.; Mereiter, K.; Kirchner, K. Kinetically Controlled Formation of Octahedral trans-Dicarbonyl Iron(II) PNP Pincer Complexes: The Decisive Role of Spin-State Changes. Organometallics 2010, 29, 4932-4942.
93. Shirobokov, O. G.; Kuzmina, L. G.; Nikonov, G. I. Nonhydride Mechanism of Metal-Catalyzed Hydrosilylation. J. Am. Chem. Soc. 2011, 133, 6487-6489.
94. Langlotz, B. K.; Wadepohl, H.; Gade, L. H. Chiral Bis(pyridylimino)isoin-doles: A Highly Modular Class of Pincer Ligands for Enantioselective Catalysis. Angew. Chem. Int. Ed. 2008, 47, 4670-4674.
95. Langer, R.; Leitus, G.; Ben-David, Y.; Milstein, D. Efficient Hydrogenation of Ketones Catalyzed by an Iron Pincer Complex. Angew. Chem. Int. Ed. 2011, 50, 2120-2124.
96. Bauer, G.; Kirchner, K. A. Well-Defined Bifunctional Iron Catalysts for the Hydrogenation of Ketones: Iron, the New Ruthenium. Angew. Chem. Int. Ed. 2011, 50, 5798-5800.
97. Casey, C. P.; Guan, H. An Efficient and Chemoselective Iron Catalyst for the Hydrogenation of Ketones. J. Am. Chem. Soc. 2007, 129, 5816-5817.
98. Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Highly Efficient Catalyst Systems Using Iron Complexes with a Tetradentate PNNP Ligand for the Asymmetric Hydrogenation of Polar Bonds. Angew. Chem. Int. Ed. 2008, 47, 940-943.
99. Trovitch, R. J.; Lobkovsky, E.; Chirik, P. J. Bis(diisopropylphosphino)-pyridine Iron Dicarbonyl, Dihydride, and Silyl Hydride Complexes. Inorg. Chem. 2006, 45, 7252-7260.
100. Dudley, M. E.; Morshed, M. M.; Brennan, C. L.; Islam, M. S.; Ahmad, M. S.; Atuu, M.-R.; Branstetter, B.; Hossain, M. M. Acid-Catalyzed Reactions of Aromatic Aldehydes with Ethyl Diazoacetate: An Investigation on the Synthesis of 3-Hydroxy-2-arylacrylic Acid Ethyl Esters. J. Org. Chem. 2004, 69, 7599-7608.
101. Benito-Garagorri, D.; Wiedermann, J.; Pollak, M.; Mereiter, K.; Kirchner, K. Iron(II) Complexes Bearing Tridentate PNP Pincer-Type Ligands as Catalysts for the Selective Formation of 3-Hydroxyacrylates from Aromatic Aldehydes and Ethyldiazoacetate. Organometallics 2007, 26, 217-222.
102. Alves, L. G.; Dazinger, G.; Veiros, L. F.; Kirchner, K. Unusual Anion Effects in the Iron-Catalyzed Formation of 3-Hydroxyacrylates from Aromatic Aldehydes and Ethyl Diazoacetate. Eur. J. Inorg. Chem. 2010, 3160-3166.
103. Sherry, B. D.; Furstner, A. The Promise and Challenge of Iron-Catalyzed Cross Coupling. Acc. Chem. Res. 2008, 41, 1500-1511.
104. Furstner, A. From Oblivion into the Limelight: Iron (Domino) Catalysis. Angew. Chem. Int. Ed. 2009, 48, 1364-1367.
105. Czaplik, W. M.; Mayer, M.; CvengroS, J.; von Wangelin, A. J. Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions. ChemSusChem 2009, 2, 396-417.
106. Jana, R.; Pathak, T. P.; Sigman, M. S. Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners. Chem. Rev. 2011, 111, 1417-1492.
107. Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M. Iron-Phosphine, -Phosphite, -Arsine, and -Carbene Catalysts for the Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents. J. Org. Chem. 2006, 71, 1104-1110.
108. Muller, G.; Klinga, M.; Leskela, M.; Rieger, B. Iron and Cobalt Complexes of a Series of Tridentate P,N,P Ligands-Synthesis, Characterization, and Application in Ethene Polymerization Reactions. Z. Anorg. Allg. Chem. 2002, 628, 2839-2846.
109. Holscher, M.; Prechtl, M. H. G.; Leitner, W. Can [M(H)2(H2)(PXP)] Pincer Complexes (M=Fe, Ru, Os; X=N, O, S) Serve as Catalyst Lead Structures for NH3 Synthesis from N2 and H2? Chem. Eur. J. 2007, 13, 6636-6643.