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Volumn 50, Issue 5, 2011, Pages 1064-1067

Rhodium-catalyzed oxidative olefination of C-H Bonds in Acetophenones and Benzamides

Author keywords

amination; Heck reaction; olefination; rhodium; stilbenes

Indexed keywords

AMINATION; KETONES; RHODIUM;

EID: 79251537123     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006222     Document Type: Article
Times cited : (411)

References (81)
  • 4
    • 79251538959 scopus 로고    scopus 로고
    • Recent reviews
    • Recent reviews
  • 5
    • 84879868832 scopus 로고    scopus 로고
    • (Ed.: M. Oestreich), Wiley, Chichester
    • The Mizoroki-Heck Reaction (Ed.:, M. Oestreich,), Wiley, Chichester, 2009
    • (2009) The Mizoroki-Heck Reaction
  • 7
    • 79251534740 scopus 로고    scopus 로고
    • For intermolecular oxidative Heck couplings, see
    • For intermolecular oxidative Heck couplings, see
  • 18
    • 77951873890 scopus 로고    scopus 로고
    • for intramolecular oxidative Heck couplings, see
    • T. Nishikata, B. H. Lipshutz, Org. Lett. 2010, 12, 1972; for intramolecular oxidative Heck couplings, see
    • (2010) Org. Lett. , vol.12 , pp. 1972
    • Nishikata, T.1    Lipshutz, B.H.2
  • 41
    • 79251578051 scopus 로고    scopus 로고
    • For examples of acetophenone directing groups in rhodium-catalyzed C-H activation processes, see
    • For examples of acetophenone directing groups in rhodium-catalyzed C-H activation processes, see
  • 50
    • 77956203593 scopus 로고    scopus 로고
    • iron-catalyzed ortho C-H arylation of protected acetophenones
    • A. J. A. Watson, A. C. Maxwell, J. M. J. Williams, Org. Lett. 2010, 12, 3856; iron-catalyzed ortho C-H arylation of protected acetophenones
    • (2010) Org. Lett. , vol.12 , pp. 3856
    • Watson, A.J.A.1    Maxwell, A.C.2    Williams, J.M.J.3
  • 52
    • 70349783716 scopus 로고    scopus 로고
    • palladium-catalyzed ortho C-H arylation of acetophenones
    • Angew. Chem. Int. Ed. 2009, 48, 2925; palladium-catalyzed ortho C-H arylation of acetophenones
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2925
  • 54
    • 79251591367 scopus 로고    scopus 로고
    • For recent examples of the use of benzamide directing groups in rhodium-catalyzed C-H activation processes, see
    • For recent examples of the use of benzamide directing groups in rhodium-catalyzed C-H activation processes, see
  • 58
    • 79251585614 scopus 로고    scopus 로고
    • Examples of powerful C-H activations utilizing acetanilides as substrates
    • Examples of powerful C-H activations utilizing acetanilides as substrates
  • 69
    • 79251589970 scopus 로고    scopus 로고
    • In contrast, benzaldehydes do not react under these conditions
    • In contrast, benzaldehydes do not react under these conditions.
  • 70
    • 79251565273 scopus 로고    scopus 로고
    • Small amounts of di-olefination products are generally observed, together with significant amounts of unreacted starting material
    • Small amounts of di-olefination products are generally observed, together with significant amounts of unreacted starting material.
  • 71
    • 79251576843 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 72
    • 79251574694 scopus 로고    scopus 로고
    • note
    • [10a,a13]
  • 73
    • 79251566798 scopus 로고    scopus 로고
    • note
    • For a recent example of the selective activation of indoles at the 2-H position through the palladium-catalyzed oxidative Heck reaction, see
  • 76
    • 79251592587 scopus 로고    scopus 로고
    • note
    • Importantly, under our standard reaction conditions, N-methylindole did not react with styrene, indicating the compatibility of the 2-H and 3-H positions of the indole with this method.
  • 77
    • 79251569002 scopus 로고    scopus 로고
    • The strategic use of the rhodium-catalyzed functionalization of acetanilides can be further illustrated by Equation (6)
    • The strategic use of the rhodium-catalyzed functionalization of acetanilides can be further illustrated by Equation (6).
  • 78
    • 79251565870 scopus 로고    scopus 로고
    • note
    • [10a] Indole products 1ab and 1ac, however, have been prepared by us with only 0.5 mola% of the rhodium catalyst precursor.
  • 79
    • 79251582558 scopus 로고    scopus 로고
    • note
    • 2], dioxane, 140a°C, 16 h).
  • 80
    • 77952578429 scopus 로고    scopus 로고
    • For a related exo cyclization in a palladium-catalyzed oxidative Heck reaction using hydroxy directing groups, see.
    • For a related exo cyclization in a palladium-catalyzed oxidative Heck reaction using hydroxy directing groups, see:, Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5916
    • Lu, Y.1    Wang, D.-H.2    Engle, K.M.3    Yu, J.-Q.4
  • 81
    • 79251581915 scopus 로고    scopus 로고
    • note
    • Utilization of the secondary amide N-Me- 3am under standard conditions resulted in the formation of the corresponding product N-Me- 4ac in 38a% yield with a reversed E/Z ratio of 7:1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.