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Volumn 125, Issue 13, 2003, Pages 3718-3719

Room-temperature Stille cross-couplings of alkenyltin reagents and functionalized alkyl bromides that possess β hydrogens

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; HYDROGEN; LEWIS ACID; TIN DERIVATIVE;

EID: 0037414261     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0344563     Document Type: Article
Times cited : (124)

References (30)
  • 3
    • 0000802361 scopus 로고    scopus 로고
    • For reviews of the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130.
    • (1997) Org. React. , vol.50 , pp. 1-652
    • Farina, V.1    Krishnamurthy, V.2    Scott, W.J.3
  • 4
    • 0242612759 scopus 로고    scopus 로고
    • Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York; Chapter 4
    • For reviews of the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Mitchell, T.N.1
  • 5
    • 0002917346 scopus 로고    scopus 로고
    • For reviews of the Stille reaction, see: (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (b) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 4. (c) Fugami, K.; Kosugi, M. Top. Curr. Chem. 2002, 219, 87-130.
    • (2002) Top. Curr. Chem. , vol.219 , pp. 87-130
    • Fugami, K.1    Kosugi, M.2
  • 8
    • 0037468071 scopus 로고    scopus 로고
    • 3-X electrophiles, see: Cardenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. See also: Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 384-387
    • Cardenas, D.J.1
  • 9
    • 0034249479 scopus 로고    scopus 로고
    • 3-X electrophiles, see: Cardenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387. See also: Luh, T.-Y.; Leung, M.-K.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
    • (2000) Chem. Rev. , vol.100 , pp. 3187-3204
    • Luh, T.-Y.1    Leung, M.-K.2    Wong, K.-T.3
  • 14
    • 0035944174 scopus 로고    scopus 로고
    • (b) Shimizu, R.; Fuchikami, T. Tetrahedron Lett. 2001, 42, 6891-6894. Fuchikami postulates, based in part on computational studies, that undesired β-hydride elimination (see Figure 1) is disfavored due to chelation of fluorine to palladium.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6891-6894
    • Shimizu, R.1    Fuchikami, T.2
  • 15
    • 0001426845 scopus 로고
    • Stille has reported couplings of α-halolactones that apparently proceed through a mixture of palladium-catalyzed and radical pathways: Simpson, J. H.; Stille, J. K. J. Org. Chem, 1985, 50, 1759-1760.
    • (1985) J. Org. Chem. , vol.50 , pp. 1759-1760
    • Simpson, J.H.1    Stille, J.K.2
  • 25
    • 0003662390 scopus 로고    scopus 로고
    • Blackie: New York
    • Tin is known to be fluorophilic. For a discussion, see: Chemistry of Tin; Smith, P. J., Ed.: Blackie: New York, 1998.
    • (1998) Chemistry of Tin
    • Smith, P.J.1
  • 27
    • 0242612758 scopus 로고    scopus 로고
    • note
    • Under these conditions, allyl-, aryl-, and alkynyltin reagents, as well as more hindered alkyl bromides, are not suitable substrates.
  • 28
    • 0242696872 scopus 로고    scopus 로고
    • note
    • 2Me]-BF4 (#15-1023).
  • 29
    • 0035961019 scopus 로고    scopus 로고
    • For other demonstrations that phosphines and the corresponding phosphonium salts can often be used interchangeably in palladium-catalyzed coupling processes, see: (a) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298. (b) Reference 1 1d.
    • (2001) Org. Lett. , vol.3 , pp. 4295-4298
    • Netherton, M.R.1    Fu, G.C.2
  • 30
    • 0035961019 scopus 로고    scopus 로고
    • Reference 1 1d
    • For other demonstrations that phosphines and the corresponding phosphonium salts can often be used interchangeably in palladium-catalyzed coupling processes, see: (a) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298. (b) Reference 1 1d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.