Method for preparing ortho-substituted aminoferrocenes

Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing

Reexamination Certificate

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C556S007000, C556S011000, C556S020000, C556S028000, C548S402000

Reexamination Certificate

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07982064

ABSTRACT:
The present disclosure relates to a method for preparing an ortho-substituted aminoferrocene comprising reacting an aminoferrocene with a Lewis acid and a lithiating reagent in the presence of an electrophile to form the ortho-substituted aminoferrocene.

REFERENCES:
patent: 2656444 (2010-05-01), None
patent: 2686357 (2010-08-01), None
patent: WO/2007/020221 (2007-02-01), None
Metallinos et al., Organic Letters, vol. 10, No. 16, pp. 3527-3530 (published on the Web Jul. 17, 2008).
Lai et al., “Intra- and Intermolecular Hydroamination of Alkynes Catalyzed by ortho-Metalated Iridium Complexes”, Organometallics, 2007, pp. 1062-1068, vol. 26(4), American Chemical Society.
Metallinos et al., “Palladium(II), Platinum(II), and Iridium(I) Complexes of 2-Phosphino-1-dimethylaminoferrocenes: A Survey of Structure and Catalysis”, Organometallics, 2009, pp. 4534-4543, vol. (28 (15), American Chemical Society.
Metallinos et al., “Aminoferrocene Lithiation by Boron Trifluoride Activation”, Organic Letters, 2008, pp. 3527-3530, vol. 10(16), American Chemical Society.
2009 CSC Abstract, “Synthesis of 2-Substituted P,N Ligands from Dimethylaminoferrocene: A Survey of Coordination Chemistry, Structure and Catalysis”, 2009.
STN Registry TM Search Results. Nov. 23, 2009.
Togni, A. Angew. Chem., Int. Ed. 1996, 35, 1475.
Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377.
Arraya's, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem.,Int. Ed. 2006, 45, 7674.
Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659.
Colacot, T. J. Chem. ReV. 2003, 103, 3101.
Miyake, Y.; Nishibayashi, Y.; Uemura, S. Synlett 2008, n/a, 1747.
Kundig, E. P.; Garcia, A. E.; Lomberget, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 2006, 45, 98.
Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389.
Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, n/a, 74.
Uemura, S.; Nishibayashi, Y. Synlett 1995, n/a, 79.
Sammakia, T.; Lathman, H. A.; Schad, D. R. J. Org. Chem. 1995, 60, 10.
Riant, O.; Samuel, O.; Kagan, H. B. J. Am. Chem. Soc. 1993, 115, 5835.
Enders, D.; Peters, R.; Lochtman, R.; Runsink, J. Synlett 1997, n/a, 1462.
Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685.
Taherpour, A. A.; Mansuri, H. R. Turk. J. Chem. 2005, 29, 317.
Rebiere, F.; Riant, O.; Ricard, L; Kagan, H. B. Angew. Chem., Int. Ed. 1993, 32, 568.
Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511.
Bolm, C.; Kesselgruber, M.; Muñiz, K.; Raabe, G. Organometallics 2000, 19, 1648.
He'rault, D.; Aelvoet, K.; Blatch, A. J.; Al-Majid, A.; Smethurst, C. A.; Whiting, A. J. Org. Chem. 2007, 72, 71.
Priego, J.; Mancheno, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. For a related process starting from a ferrocenyl oxazoline, see: Salter, R.; Pickett, T. E.; Richards, C. J. Tetrahedron:Asymmetry 1998, 9, 4239.
Bertogg, A.; Camponovo, F.; Togni, A. Eur. J. Inorg. Chem. 2005, n/a, 347.
Bertogg, A.; Togni, A. Organometallics 2006, 25, 622.
Buszek, K. R.; Brown, N. J. Org. Chem. 2007, 72, 3125.
Samec, J. S. M.; Backvall, J. E. Chem. Eur. J. 2002, 8, 2955.
Britton, W. E.; Kashyap, R.; El-Hashash, M.; El-Kady, M.; Herberhold, M. Organometallics 1986, 5, 1029.
Sato, M.; Ebine, S. Synthesis 1981, n/a, 472.
Pearson, M. S.; Jensky, B. J.; Greer, F. X.; Hagstrom, J. P.; Wells, N. M.; J. Org. Chem. 1978, 43, 4617.
Fanta, P. E. Synthesis 1974, n/a, 9.
Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172.
Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409.
Cabello, N.; Kizirian, J.-C.; Gille, S.; Alexakis, A.; Bernardinelli, G.; Pinchard, L.; Caille, J.-C. Eur. J. Org. Chem. 2005, n/a, 483.
Fox, D. J.; Pedersen, D. S.; Warren, S. Org. Biomol. Chem. 2006, 4, 3102.
Mealey, M. J.; Luderer, M. R.; Bailey, W. F.; Sommer, M. B. J. Org. Chem. 2004, 69, 6042.
O'Brien, P. Chem. Commun. 2008, 655.
Black, P.J.; Edwards, M.G.; Williams, J. M. J. Eur. J. Org. Chem. 2006, 19, 4367.
Metallinos, C. et al., “Asymmetric Lithiation of Boron Trifluoride-Activated Amino-ferrocenes: An Experimental and Computational Investigation” Adv Synth Catal. 2010, 352, 1967-1982.
Metallinos, C et al., “Asymmetric hydrogenation of alkene with planar chiral 2-phosphino-1-aminoferrocene-iridium(I) complexes”, Journal of Organometallic Chemistry 696 (2011) 141-149.
He, J.; Zheng, J.; Liu, J.; She, X.; Pan, X. Org. Lett. 2006, 8, 4637.
Hareau, G. P. J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.

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