Convenient palladium-catalyzed preparation of primary anilines using a fluorous benzophenone imine reagent

Synlett

Volumn , Issue 5, 2004, Pages 841-845

  Cioffi, Christopher L ^a   Berlin, Michael L ^a   Herr, R Jason ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

Amination; Arylation; Cross coupling; Fluorous; Palladium catalyzed

Indexed keywords

AMMONIA; ANILINE DERIVATIVE; BENZOPHENONE DERIVATIVE; HALIDE; PALLADIUM; REAGENT;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHROMATOGRAPHY; HYDROLYSIS; PURIFICATION;

EID: 1942456883     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820011     Document Type: Article

References (44)

1. For recent reviews on palladium-catalyzed aryl amination methods, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (d) Hartwig, J. F. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
2. For recent reviews on palladium-catalyzed aryl amination methods, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (d) Hartwig, J. F. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
3. For recent reviews on palladium-catalyzed aryl amination methods, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (d) Hartwig, J. F. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
4. For recent reviews on palladium-catalyzed aryl amination methods, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125. (d) Hartwig, J. F. Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2000.
5. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
6. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
7. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
8. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
9. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
10. Palladium-catalyzed aryl aminations utilizing ammonia surrogates to prepare primary anilines: (a) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367. (b) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313. (c) Hori, K.; Mori, M. J. Am. Chem. Soc. 1998, 120, 7651. (d) Lim, C. W.; Lee, S. Tetrahedron 2000, 56, 5131. (e) Lee, S.; Jørgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729. (f) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417. (g) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885. (h) Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689.
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