Low Valent, Low Coordinate Complexes Using Bulky Ligands
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1 Low Valent, Low Coordinate Complexes Using Bulky Ligands 01/14/2015 Presented By Michael C. Young
2 Topics Two and three coordinate low valent complexes of Ni Work by the Hillhouse Group Bulky m-terphenyl isonitrile ligands for low coordinate transition metal complexes Work by the Figueroa Group Low coordinate complexes of Fe and Co Work by the Betley Group
3 Monomeric Terminal Ni(II)-Imido Impetus: At the time there was a dearth of examples of nickel complexes with hard imido ligands. To prevent dimerization, it was desirable to use both a bulky phosphine ligand as well as a bulky nitrogen. 3 5 Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc., 2001, 123, 4623.
4 Monomeric Ni(II)-Phosphinidene Similarly, there was no good example of a phosphinidene complex, and the imido synthesis suggested the analogous phosphinidene should be easily obtained. 5 Melenkivitz, R.; Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc., 2002, 124,
5 Ni(II)-Carbene and Reactions Although Ni(II)-diazo complexes were known, it should be possible to extrude nitrogen to give a carbene Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc., 2002, 124, 9976.
6 Ni(II)-Imido Transfer Reactions The formed imidos can be used for nitrene transfer reactions. Mindiola, D. J.; Hillhouse, G. L. Chem. Commun., 2002, 1840.
7 Ni(II)=X Group Transfer with C2H4 All of the Ni(II)=X species thus far discussed can react with olefins Waterman, R.; Hillhouse, G. L. J. Am. Chem. Soc., 2003, 125,
8 Ni(II)=P Transfer with Alkynes Waterman, R.; Hillhouse, G. L. Organometallics, 2003, 22, 5182.
9 Unsaturated Ni(I) vs Ni(II)-C Species Organolithiums can also be added to Ni(I) to give monoalkyls Kitiachvili, K. D.; Mindiola, D. J.; Hillhouse, G. L. Organometallics, 2004, 126,
10 Ni(0) Coordination of N2 and NO N2 binds in a side-on fashion at low temperature Iluc, V. M.; Miller, A. J. M.; Hillhouse, G. L. Organometallics, 2005, 127, 5091.
11 Ni(0) Coordination of N3 Unsurprisingly, azides can also form stable adducts with this complex. Waterman, R.; Hillhouse, G. L. J. Am. Chem. Soc., 2008, 130,
12 Dicoordinate Ni(I) and Reactions Laskowski, C. A.; Hillhouse, G. L. J. Am. Chem. Soc., 2008, 130,
13 Insertion into Ni(II)-Alkyl Bonds Curley, J. J.; Kitiachvili, K. D.; Waterman, R.; Hillhouse, G. L. Organometallics, 2009, 28, 2568.
14 Ni-CarbeneTransfer Harrold, N. D.; Waterman, R.; Hillhouse, G. L.; Cundari, T. R. J. Am. Chem. Soc., 2009, 131,
15 Catalytic Route to Diimides Laskowski, C. A.; Hillhouse, G. L. Organometallics, 2009, 28, 6114.
16 Catalytic Route to Diimides Laskowski, C. A.; Hillhouse, G. L. Organometallics, 2009, 28, 6114.
17 Towards a Ni(II)-Silylene Complex Iluc, V. M.; Hillhouse, G. L. J. Am. Chem. Soc., 2010, 132,
18 Reactions of Ni(0) and Ni(I) with CX 2 Anderson, J. S.; Iluc, V. M.; Hillhouse, G. L. Inorg. Chem., 2010,
19 Ni(I)-XHR to Ni(II)=X Radical Pathway Iluc, V. M.; Hillhouse, G. L. J. Am. Chem. Soc., 2010, 132,
20 Dicoordinate Ni(II) Complexes Laskowski, C. A.; Miller, A. J. M.; Hillhouse, G. L.; Cundari, T. R. J. Am. Chem. Soc., 2011, 133, 771.
21 Ni(II)-Carbene-Bridged Dimers Laskowski, C. A.; Hillhouse, G. L. Chem. Sci., 2010, 2, 321.
22 Ni(III)-Imido Complex A terminal Ni(III)-imido should be exceptionally reactive and therefore unstable. Iluc, V. M.; Miller, A. J. M.; Anderson, J. S.; Monreal, M. J.; Mehn, M. P.; Hillhouse, G. L. J. Am. Chem. Soc., 2011, 133,
23 Bis-NHC-Ni Complexes Harrold, N. D.; Hillhouse, G. L. Chem. Sci., 2013, 4, 4011.
24 Bis-NHC-Ni Complexes Harrold, N. D.; Hillhouse, G. L. Chem. Sci., 2013, 4, 4011.
25 Towards NHC-Ni(I) Alkyl Complexes Laskowski, C. A.; Bungum, D. J.; Baldwin, S. M.; Del Ciello, S. A.; Illuc, V. M.; Hillhouse, G. L. J. Am. Chem. Soc., 2013, 135,
26 3-Coordinate Ni(II) Carbenes Iluc, V. M.; Hillhouse, G. L. J. Am. Chem. Soc., 2014, 136, 6479.
27 Isocyano Ligands and Cu(I) Fox, B. J.; Sun, Q. Y.; DiPasquale, A. G.; Fox, A. R.; Rheingold, A. L.; Figueroa, J. S. Inorg. Chem., 2009, 131,
28 Isocyano Ligands with Ni(0) Fox, B. J.; Millard, M. D.; DiPasquale, A. G.; Rheingold, A. L.; Figueroa, J. S. Angew. Chem., Int. Ed., 2009, 48, Emerich, B. M.; Moore, C. E.; Fox, B. J.; Rheingold, A. L.; Figueroa, J. S. Organometallics, 2011, 30, 2598.
29 2-Coordinate Pd(0) with Isocyano Ligands Labios, L. A.; Millard, M. D.; Rheingold, A. L.; Figueroa, J. S. J. Am. Chem. Soc., 2009, 131,
30 Ligand C H Amination with Fe(II) Replacing Fe(II) with Zn(II) shuts down the reaction. King, E. R.; Betley, T. A. Inorg. Chem., 2009, 48, 2361.
31 Complexes of Dipyrromethane King, E. R.; Betley, T. A. J. Am. Chem. Soc., 2009, 131,
32 Complexes of Dipyrromethane King, E. R.; Hennessy, E. T.; Betley, T. A. J. Am. Chem. Soc., 2011, 133, 4917.
33 Complexes of Dipyrromethane The reaction of 1 with adamantyl amine in toluene gives 6.7 turnover (amine 95%, imine 2.8%, adamantylamine 1.8%). Product inhibited by anything that outcompetes azide for chelation. KIE is consistent with H abstraction being the RDS. King, E. R.; Hennessy, E. T.; Betley, T. A. J. Am. Chem. Soc., 2011, 133, 4917.
34 Complexes of Dipyrromethane King, E. R.; Hennessy, E. T.; Betley, T. A. J. Am. Chem. Soc., 2011, 133, 4917.
35 Electronic Perturbation of Ligands Scharf, A. B.; Betley, T. A. Inorg. Chem., 2011, 50, 6837.
36 Co(III) Complexes of Dipyrromethane King, E. R.; Sazama, G. T.; Betley, T. A. J. Am. Chem. Soc., 2012, 134,
37 Intramolecular Cyclization of Alkyl Azides Based on the previous results, the group next wanted to explore the substrate scope of their nitrene insertion into aliphatic C H bonds. Hennessy, E. T.; Betley, T. A. Science, 2013, 340, 591.
38 Intramolecular Cyclization of Alkyl Azides Hennessy, E. T.; Betley, T. A. Science, 2013, 340, 591.
39 Intramolecular Cyclization of Alkyl Azides Hennessy, E. T.; Betley, T. A. Science, 2013, 340, 591.
40 Intramolecular Cyclization of Alkyl Azides As the substrates become more complex, so too are the product(s). Hennessy, E. T.; Betley, T. A. Science, 2013, 340, 591.
41 Intramolecular Cyclization of Alkyl Azides Hennessy, E. T.; Betley, T. A. Science, 2013, 340, 591.
42 Thank you for your attention! Accessed 01/14/2015.
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