Organometallics
Cartesian coordinates for the calculated structure of 5
Article
L. Nature 2015, 526, 96−99. (g) Russell, S. K.; Lobkovsky, E.; Chirik,
P. J. J. Am. Chem. Soc. 2011, 133, 8858−8851. (h) Hoyt, J. M.;
Sylvester, K. T.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2013,
135, 4862−4877.
(6) For reviews treating noninnocent ligands, see: (a) Blanchard, S.;
̀
Derat, E.; Desage-El Murr, M.; Fensterbank, L.; Malacria, M.; Mouries-
AUTHOR INFORMATION
Corresponding Author
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Mansuy, V. Eur. J. Inorg. Chem. 2012, 2012, 376−389. (b) Luca, O. R.;
Crabtree, R. H. Chem. Soc. Rev. 2013, 42, 1440−1459. (c) Khusnutdi-
nova, J. R.; Milstein, D. Angew. Chem. Int. Ed. 2015, 54, 2−40.
(7) Selected references of P-based iron(0) complexes: (a) Rathke, J.
W.; Muetterties, E. L. J. Am. Chem. Soc. 1975, 97, 3272−3273.
(b) Tolman, C. A.; Ittel, S. D.; English, A. D.; Jesson, J. P. J. Am. Chem.
Soc. 1978, 100, 4080−4089. (c) Ittel, S. D.; Van-Catledge, F. A.;
Jesson, J. P. J. Am. Chem. Soc. 1979, 101, 3874−3884. (d) Lindner, E.;
Schauss, E.; Hiller, W.; Fawzi, R. Angew. Chem., Int. Ed. Engl. 1984, 23,
711−712. (e) Boncella, J. M.; Green, M. L. H.; O’Hare, D. J. Chem.
Soc., Chem. Commun. 1986, 8, 618−619. (f) Baker, M. V.; Field, L. D.
J. Am. Chem. Soc. 1986, 108, 7433−7434. (g) Zenneck, U.; Frank, W.
Angew. Chem., Int. Ed. Engl. 1986, 25, 831−833. (h) Hoberg, H.; Jenni,
ORCID
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We gratefully acknowledge IFP Energies nouvelles, the TGIR-
RMN-THC Fr3050 CNRS, the European Research Council
under the European Union’s Horizon 2020 Research and
Innovation Programme (Grant 648974 “P-MEM-NMR”), and
the European Union’s Seventh Framework Programme (FP7-
PEOPLE-2012-ITN 317127 “pNMR”) for support.
K.; Raabe, E.; Kruger, C.; Schroth, G. J. Organomet. Chem. 1987, 320,
̈
325−338. (i) Brookhart, M.; Chandler, W. A.; Mister, A. C.; Santini,
C. C.; White, P. S. Organometallics 1992, 11, 1263−1274.
(j) Elschenbroich, C.; Nowotny, M.; Behrendt, A.; Harms, K.;
Wocadlo, S.; Pebler, J. J. Am. Chem. Soc. 1994, 116, 6217−6219.
(k) Hirano, M.; Akita, M.; Morikita, T.; Kubo, H.; Fukuoka, A.;
Komiya, S. J. Chem. Soc., Dalton Trans. 1997, 19, 3453−3458.
(l) Kubo, H.; Hirano, M.; Komiya, S. J. Organomet. Chem. 1998, 556,
89−95. (m) Bennett, M. A.; Ditzel, E. J.; Hunter, A. D.; Khan, K.;
Kopp, M. R.; Neumann, H.; Robertson, G. B.; Zech, H. J. Chem. Soc.,
Dalton Trans. 2000, 11, 1733−1741. (n) Gilbert-Wilson, R.; Field, L.
D.; Colbran, S. B.; Bhadbhade, M. M. Inorg. Chem. 2013, 52, 3043−
3053.
REFERENCES
■
(1) (a) Bauer, I.; Knolker, H.-J. Chem. Rev. 2015, 115, 3170−3387.
̈
(b) Burcher, B.; Breuil, P.-A. R.; Magna, L.; Olivier-Bourbigou, H. In
Iron Catalysis II; Bauer, E., Ed.; Springer International: Cham,
Switzerland, 2015; Vol. 50, pp 217−258.
(2) (a) Lavallo, V.; El-Batta, A.; Bertrand, G.; Grubbs, R. H. Angew.
Chem., Int. Ed. 2011, 50, 268−271. (b) Ung, G.; Rittle, J.;
Soleilhavoup, M.; Bertrand, G.; Peters, J. C. Angew. Chem., Int. Ed.
2014, 53, 8427−8431. (c) Danopoulos, A. A.; Wright, J. A.;
Motherwell, W. B. Chem. Commun. 2005, 784−786. (d) Brennessel,
W. W.; Jilek, R. E.; Ellis, J. E. Angew. Chem., Int. Ed. 2007, 46, 6132−
6136. (e) Werncke, C. G.; Bunting, P. C.; Duhayon, C.; Long, J. R.;
Bontemps, S.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2015, 54, 245−
248. (f) Zadrozny, J. M.; Xiao, D. J.; Atanasov, M.; Long, G. J.;
Granjean, F.; Neese, F.; Long, J. R. Nat. Chem. 2013, 5, 577−581.
(g) Danopoulos, A. A.; Braunstein, P.; Monakhov, K. Yu.; van Leusen,
(8) Bart, S. C.; Hawrelak, E. J.; Lobkovsky, E.; Chirik, P. J.
Organometallics 2005, 24, 5518−5527.
(9) (a) Hoberg, H.; Jenni, K. J. Organomet. Chem. 1986, 301, C59−
C61. (b) Bleeke, J. R.; Wittenbrink, R. J. J. Organomet. Chem. 1991,
405, 121−132. (c) Geier, S.; Goddard, R.; Holle, S.; Jolly, P. W.;
Kruger, C.; Lutz, F. Organometallics 1997, 16, 1612−1620. (d) Hoberg,
H.; Jenni, K.; Angermund, K.; Kruger, C. Angew. Chem., Int. Ed. Engl.
̈
̈
́
J.; Kogerler, P.; Clemancey, M.; Latour, J.-M.; Benayad, A.; Tromp,
̈
1987, 26, 153−155.
(10) Casitas, A.; Krause, H.; Goddard, R.; Furstner, A. Angew. Chem.,
̈
Int. Ed. 2015, 54, 1521−1526.
(3) (a) Hoyt, J. M.; Schmidt, V. A.; Tondreau, A. M.; Chirik, P. J.
Science 2015, 349, 960−963. (b) Anderson, J. S.; Rittle, J.; Peters, J. C.
Nature 2013, 501, 84−88. (c) Creutz, S. E.; Peters, J. C. J. Am. Chem.
Soc. 2014, 136, 1105−1115. (d) Ung, G.; Peters, J. C. Angew. Chem.,
(11) Zhang, H.; Ouyang, Z.; Liu, Y.; Zhang, Q.; Wang, L.; Deng, L.
Angew. Chem., Int. Ed. 2014, 53, 8432−8436.
(12) (a) Marciniec, B.; Kownacki, I.; Taylor, R. Appl. Catal., A 2014,
486, 230−238. (b) Kownacka, A.; Kownacki, I.; Kubicki, M.;
Marciniec, B.; Taylor, R. J. Organomet. Chem. 2014, 750, 132−139.
(c) Marciniec, B.; Kownacka, A.; Kownacki, I.; Hoffmann, M.; Taylor,
R. J. Organomet. Chem. 2015, 791, 58−65.
Int. Ed. 2015, 54, 532−535. (e) Boddien, A.; Loges, B.; Gartner, F.;
̈
Toborg, C.; Fumino, K.; Junge, H.; Ludwig, R.; Beller, M. J. Am. Chem.
Soc. 2010, 132, 8924−8934. (f) Furstner, A.; Majima, K.; Martín, R.;
̈
Krause, H.; Kattnig, E.; Goddard, R.; Lehmann, C. W. J. Am. Chem.
(13) (a) Avent, A. G.; Lappert, M. F.; MacBeath, C. J. Organomet.
Soc. 2008, 130, 1992−2004. (g) Furstner, A.; Martín, R.; Krause, H.;
̈
Chem. 1995, 502, 163−167. (b) Vollmuller, F.; Krause, J.; Klein, S.;
̈
Seidel, G.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130,
8773−8787. (h) Bart, S. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem.
Soc. 2004, 126, 13794−13807. (i) Wang, C.; Li, X.; Wu, F.; Wan, B.
Angew. Chem., Int. Ed. 2011, 50, 7162−7166.
Magerlein, W.; Beller, M. Eur. J. Inorg. Chem. 2000, 2000, 1825−1832.
̈
(c) Harkal, S.; Jackstell, R.; Nierlich, F.; Ortmann, D.; Beller, M. Org.
Lett. 2005, 7, 541−544.
(14) (a) Weber, S. R.; Brintzinger, H. H. J. Organomet. Chem. 1977,
(4) McNeill, E.; Ritter, T. Acc. Chem. Res. 2015, 48, 2330−2343.
(5) Selected examples of low-oxidation-state iron complexes
stabilized by nitrogen-based ligands: (a) Stoian, S. A.; Yu, Y.; Smith,
127, 45−54. (b) Funhoff, A.; Schaufele, H.; Zenneck, U. J. Organomet.
Chem. 1988, 345, 331−339. (c) Schmidt, U.; Zenneck, U. J.
Organomet. Chem. 1992, 440, 187−190.
̈
J. M.; Holland, P. L.; Bominaar, E. L.; Munck, E. Inorg. Chem. 2005,
̈
(15) (a) Breschi, C.; Piparo, L.; Pertici, P.; Caporusso, A. M.; Vitulli,
G. J. Organomet. Chem. 2000, 607, 57−63. (b) Saino, N.; Kogure, D.;
Kase, K.; Okamoto, S. J. Organomet. Chem. 2006, 691, 3129−3136.
(c) Liu, Y.; Yan, X.; Yang, N.; Xi, C. Catal. Commun. 2011, 12, 489−
492. (d) Lipschutz, M. I.; Chantarojsiri, T.; Dong, Y.; Tilley, D. T. J.
Am. Chem. Soc. 2015, 137, 6366−6372.
44, 4915−4922. (b) Yu, Y.; Smith, J. M.; Flaschenriem, C. J.; Holland,
P. L. Inorg. Chem. 2006, 45, 5742−5751. (c) Smith, J. M.; Sadique, A.
R.; Cundari, T. R.; Rogers, K. R.; Lukat-Rodgers, G.; Lachicotte, R. J.;
Flaschenriem, C. J.; Vela, J.; Holland, P. L. J. Am. Chem. Soc. 2006, 128,
756−769. (d) Chiang, K. P.; Scarborough, C. C.; Horitani, M.; Lees,
N. S.; Ding, K.; Dugan, T. R.; Brenessel, W. W.; Bill, E.; Hoffman, B.
M.; Holland, P. L. Angew. Chem., Int. Ed. 2012, 51, 3658−3662.
(e) Rodriguez, M. M.; Stubbert, B. D.; Scarborough, C. C.; Brennessel,
W. W.; Bill, E.; Holland, P. L. Angew. Chem., Int. Ed. 2012, 51, 8247−
8250. (f) Coric, I.; Mercado, B. Q.; Bill, E.; Vinyard, D. J.; Holland, P.
(16) Hata, G.; Kondo, H.; Miyake, A. J. Am. Chem. Soc. 1968, 90,
2278−2281.
(17) Vaara, J.; Rouf, S. A.; Mares,
̌
J. J. Chem. Theory Comput. 2015,
11, 4840−4849.
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