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Volumn 63, Issue 23, 1998, Pages 8407-8410

Palladium-catalyzed amination of aryl bromides utilizing arene-chromium complexes as ligands

Author keywords

[No Author keywords available]

Indexed keywords

2 DIPHENYLPHOSPHINO ALPHA PHENYLETHYLAMINE; ALPHA PHENYLETHYL METHYL ETHER DERIVATIVE; BROMIDE; CHROMIUM; HALIDE; METHYL ALPHA (2 DIPHENYLPHOSPHINO)PHENYLETHYL ETHER; N,N DIMETHYL ALPHA (2 DIPHENYLPHOSPHINO)PHENYLETHYLAMINE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

EID: 0032514859     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981327+     Document Type: Article
Times cited : (39)

References (32)
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    • For representative review and references see: (a) Hartwig, J. F. Synlett 1997, 329-340. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267. (c) Louie, J. L.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218. (e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. (f) Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
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    • For representative review and references see: (a) Hartwig, J. F. Synlett 1997, 329-340. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267. (c) Louie, J. L.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218. (e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. (f) Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
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    • For representative review and references see: (a) Hartwig, J. F. Synlett 1997, 329-340. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267. (c) Louie, J. L.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218. (e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. (f) Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7217-7218
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    • For representative review and references see: (a) Hartwig, J. F. Synlett 1997, 329-340. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267. (c) Louie, J. L.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218. (e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. (f) Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7215-7216
    • Wolfe, J.P.1    Wagaw, S.2    Buchwald, S.L.3
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    • For representative review and references see: (a) Hartwig, J. F. Synlett 1997, 329-340. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267. (c) Louie, J. L.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218. (e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. (f) Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1348-1350
    • Guram, S.1    Rennels, R.A.2    Buchwald, S.L.3
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    • Some representative references include the following: (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374. (c) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (d) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214. (e) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernàndez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
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    • Guram, A.S.1    Buchwald, S.L.2
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    • Some representative references include the following: (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374. (c) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (d) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214. (e) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernàndez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
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    • Hartwig, J.F.1    Paul, F.2
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    • 0030760535 scopus 로고    scopus 로고
    • Some representative references include the following: (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374. (c) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (d) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214. (e) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernàndez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8451-8458
    • Wagaw, S.1    Rennels, R.A.2    Buchwald, S.L.3
  • 11
    • 0032515443 scopus 로고    scopus 로고
    • Some representative references include the following: (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374. (c) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (d) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214. (e) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernàndez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 213-214
    • Singer, R.A.1    Sadighi, J.P.2    Buchwald, S.L.3
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    • 0032481408 scopus 로고    scopus 로고
    • Some representative references include the following: (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374. (c) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458. (d) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214. (e) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernàndez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827-828.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 827-828
    • Mann, G.1    Hartwig, J.F.2    Driver, M.S.3    Fernàndez-Rivas, C.4
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    • For some reviews see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 922-940. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, pp 99-133. (c) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 1-57. (d) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 195-245.
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    • Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
    • For some reviews see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 922-940. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, pp 99-133. (c) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 1-57. (d) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 195-245.
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    • Solladié-Cavallo, A.1
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    • 0001772726 scopus 로고
    • Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
    • For some reviews see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 922-940. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, pp 99-133. (c) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 1-57. (d) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 195-245.
    • (1991) Advances in Metal-Organic Chemistry , vol.2 , pp. 1-57
    • Davies, S.G.1    Coote, S.J.2    Goodfellow, C.L.3
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    • 0000958965 scopus 로고
    • Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT
    • For some reviews see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 922-940. (b) Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, pp 99-133. (c) Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 1-57. (d) Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 2, pp 195-245.
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    • note
    • w = 0.044.
  • 31
    • 15644372891 scopus 로고    scopus 로고
    • Surprisingly, the chelated monodentate ligand 12 produced the corresponding amine compound for the coupling reaction of p-benzoyl bromobenzene with morpholine in 88% yield
    • Surprisingly, the chelated monodentate ligand 12 produced the corresponding amine compound for the coupling reaction of p-benzoyl bromobenzene with morpholine in 88% yield.


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