Palladium-Catalyzed Amination of Aryl Bromides: Use of Phosphinoether Ligands for the Efficient Coupling of Acyclic Secondary Amines

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1568-1569

  Marcoux, Jean François ^a   Wagaw, Seble ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001674239     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622946     Document Type: Article

References (25)

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5. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
6. 2 (containing ca. 0.25 equiv of DMF) prepared accordingly to the procedure in ref in 5a gave similar results. For this procedure, see: Davies, J. A.; Hartley, F. R.; Murray, S. G. J. Chem. Soc., Dalton Trans. 1979, 1705-1708.
7. For application in solid-phase synthesis, see: (a) Willoughby, C. A.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 7181-7184. (b) Ward, D.; Farina, V. Tetrahedron Lett. 1996, 37, 6993-6996.
8. For application in solid-phase synthesis, see: (a) Willoughby, C. A.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 7181-7184. (b) Ward, D.; Farina, V. Tetrahedron Lett. 1996, 37, 6993-6996.
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10. Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902 and references cited therein.
11. Marcoux, J.-F.; Wolfe, J. P.; Buchwald, S. L. Unpublished results.
12. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138- 1139.
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18. Details of the X-ray determination will be fully described elsewhere. The ORTEP diagram is included in the Supporting Information. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
19. (a) Kapteijn, G. M.; Grove, D. M.; Kooijman, H.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Inorg. Chem. 1996, 35, 526-533.
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22. 3 at room temperature showed that the methoxy protons were shifted by 1.1 ppm downfield compared to the uncomplexed PPF- OMe.
23. Even though we believe that ligand 5 is chelating most of the time, this does not preclude the possibility that keys steps are occurring via a three-coordinate palladium intermediate.
24. 3/Pd catalytic system, see: Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633.
25. For a discussion about the factors that influence the rate of reductive elimination of transition-metal complexes, see: Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; p 27 and references cited therein.