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Volumn 23, Issue 9, 2004, Pages 2114-2123

Comparing nickel- and palladium-catalyzed Heck reactions

Author keywords

[No Author keywords available]

Indexed keywords

ENERGY BARRIERS; HECK REACTIONS; OXIDATIVE ADDITION; REDUCTIVE PATHWAY;

EID: 2442609566     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034067h     Document Type: Article
Times cited : (177)

References (70)
  • 58
    • 2442537623 scopus 로고
    • An alternative mechanism for oxidative addition (i.e., a mechanism via ate complexes) has been investigated by Siegbahn et al. (see: Siegbahn, P. E. M.; Blomberg, M. R. A. Catal. Met. Complexes 1995, 18, 15.
    • (1995) Catal. Met. Complexes , vol.18 , pp. 15
    • Siegbahn, P.E.M.1    Blomberg, M.R.A.2
  • 60
    • 2442600897 scopus 로고    scopus 로고
    • note
    • The product of oxidative addition could isomerize to a trans complex. However, we only considered the cis complex in this study to simplify the calculations.
  • 62
    • 0032516334 scopus 로고    scopus 로고
    • Deeth et al. proposed that β-hydrogen elimination did not occur in the Heck reactions because the agostic hydrogen is kinetically the more acidic one and hence preferentially deprotonated. (See: (a) Deeth, R. J.; Smith, A.; Hii, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229. (b) Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim, Acta 2002, 84, 3043.) In disagreement with Death's proposal, our results suggest that β-elimination is the preferential pathway. It is noteworthy that others have also proposed the β-hydrogen elimination pathway in related reactions. Some also found that β-hydrogen elimination occurs more easily in the Pd complex than in the Ni complex (see: Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107).
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3229
    • Deeth, R.J.1    Smith, A.2    Hii, K.K.3    Brown, J.M.4
  • 63
    • 0035183650 scopus 로고    scopus 로고
    • Deeth et al. proposed that β-hydrogen elimination did not occur in the Heck reactions because the agostic hydrogen is kinetically the more acidic one and hence preferentially deprotonated. (See: (a) Deeth, R. J.; Smith, A.; Hii, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229. (b) Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim, Acta 2002, 84, 3043.) In disagreement with Death's proposal, our results suggest that β-elimination is the preferential pathway. It is noteworthy that others have also proposed the β-hydrogen elimination pathway in related reactions. Some also found that β-hydrogen elimination occurs more easily in the Pd complex than in the Ni complex (see: Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107).
    • (2002) Helv. Chim, Acta , vol.84 , pp. 3043
    • Hii, K.K.1    Claridge, T.D.W.2    Brown, J.M.3    Smith, A.4    Deeth, R.J.5
  • 64
    • 0033432361 scopus 로고    scopus 로고
    • Deeth et al. proposed that β-hydrogen elimination did not occur in the Heck reactions because the agostic hydrogen is kinetically the more acidic one and hence preferentially deprotonated. (See: (a) Deeth, R. J.; Smith, A.; Hii, K. K.; Brown, J. M. Tetrahedron Lett. 1998, 39, 3229. (b) Hii, K. K.; Claridge, T. D. W.; Brown, J. M.; Smith, A.; Deeth, R. J. Helv. Chim, Acta 2002, 84, 3043.) In disagreement with Death's proposal, our results suggest that β-elimination is the preferential pathway. It is noteworthy that others have also proposed the β-hydrogen elimination pathway in related reactions. Some also found that β-hydrogen elimination occurs more easily in the Pd complex than in the Ni complex (see: Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107).
    • (1999) Top. Catal. , vol.7 , pp. 107
    • Musaev, D.G.1    Morokuma, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.