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Volumn 72, Issue 8, 2007, Pages 2816-2822

Synthesis and characterization of R2PN=P(iBuNCH 2CH2)3N: A new bulky electron-rich phosphine for efficient Pd-assisted Suzuki-Miyaura cross-coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; CATALYST ACTIVITY; ELECTRONS; IODINE; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 34247186439     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062452l     Document Type: Article
Times cited : (63)

References (63)
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    • For examples of industrially feasible palladium-catalyzed cross-coupling reactions see: (a) Beller, M.; Zapf, A. Chem. Commun. 2005, 431 and references cited therein.
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    • and references cited therein
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  • 5
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    • For the pioneering work of Suzuki and Miyaura, see: a
    • For the pioneering work of Suzuki and Miyaura, see: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
    • (1999) J. Organomet. Chem , vol.576 , pp. 147
    • Suzuki, A.1
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    • Diederich, F, Stang, P. J, Eds, Wiley-VCH: New York, Chapter 2, pp, and references cited therein
    • (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 2, pp 49-97, and references cited therein.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 49-97
    • Suzuki, A.1
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    • (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457 and references cited therein.
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    • For additional references reporting Suzuki-Miyaura cross-coupling reactions, see Supporting Information
    • For additional references reporting Suzuki-Miyaura cross-coupling reactions, see Supporting Information.
  • 16
    • 0000718373 scopus 로고    scopus 로고
    • For the application of Suzuki coupling in the synthesis of liquid crystals, see: a, and references cited therein
    • For the application of Suzuki coupling in the synthesis of liquid crystals, see: (a) Pu, L. Chem. Rev. 1998, 98, 2405 and references cited therein.
    • (1998) Chem. Rev , vol.98 , pp. 2405
    • Pu, L.1
  • 19
    • 0000795317 scopus 로고    scopus 로고
    • The key step in the synthesis of Losartan is a Suzuki cross-coupling reaction: Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151.
    • The key step in the synthesis of Losartan is a Suzuki cross-coupling reaction: Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151.
  • 20
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    • For reviews on Sartans and Losartan, see: a
    • For reviews on Sartans and Losartan, see: (a) Birkenhager, W. H.; de Leeuw, P. W. J. Hypertens. 1999, 17, 873.
    • (1999) J. Hypertens , vol.17 , pp. 873
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  • 23
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    • For some recent references in ligandless Suzuki couplings reactions, see: a, and references cited therein
    • For some recent references in ligandless Suzuki couplings reactions, see: (a) Korolev, D. N.; Bumagin, N. A. Tetrahedron Lett. 2006, 47, 4225 and references cited therein.
    • (2006) Tetrahedron Lett , vol.47 , pp. 4225
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  • 24
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    • and references cited therein
    • (b) Liu, L.; Zhang, Y.; Xin, B. J. Org. Chem. 2006, 71, 3994 and references cited therein.
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    • Littke, A.F.1    Fu, G.C.2
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    • For reviews on proazaphosphatranes, see: a
    • For reviews on proazaphosphatranes, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 223, 1.
    • (2002) Top. Curr. Chem , vol.223 , pp. 1
    • Verkade, J.G.1
  • 39
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    • For [Pd]/proazaphosphatrane-catalyzed Suzuki cross-coupling, see: Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
    • For [Pd]/proazaphosphatrane-catalyzed Suzuki cross-coupling, see: Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
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  • 61
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    • The low reactivity of aryl chlorides in cross-coupling reactions is generally ascribed to their reluctance to oxidatively add to Pd(0, Aryl halides that bear an electron-withdrawing group oxidatively add to Pd(0) more readily than do the corresponding unsubstituted aryl halides. For discussions, see: (a) Grushin, V. V, Alper, H. Chem. Rev. 1994, 94, 1047
    • The low reactivity of aryl chlorides in cross-coupling reactions is generally ascribed to their reluctance to oxidatively add to Pd(0). Aryl halides that bear an electron-withdrawing group oxidatively add to Pd(0) more readily than do the corresponding unsubstituted aryl halides. For discussions, see: (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.


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