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Volumn 2, Issue 3, 2011, Pages 544-551

Ru-catalyzed activation of sp3 C-O bonds: O- to N-alkyl migratory rearrangement in pyridines and related heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLES; NOVEL STRATEGIES; RU CATALYSIS;

EID: 79955636570     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c0sc00498g     Document Type: Article
Times cited : (79)

References (89)
  • 10
    • 78650506132 scopus 로고    scopus 로고
    • DOI: 10.1021/ar100082d. For selected examples of C-OR bond activation involving p-allyl chemistry, see
    • D.-G. Yu, B.-J. Li and Z.-J. Shi, Acc. Chem. Res., 2010, DOI: 10.1021/ar100082d. For selected examples of C-OR bond activation involving p-allyl chemistry, see:
    • (2010) Acc. Chem. Res
    • Yu, D.-G.1    Li, B.-J.2    Shi, Z.-J.3
  • 18
    • 79955581003 scopus 로고    scopus 로고
    • Note
    • For selected examples of C-OR bond activation involving Ni-catalyzed Kumada couplings.
  • 34
    • 79955585975 scopus 로고    scopus 로고
    • For selected examples of natural products with N-alkylpyridone rings
    • For selected examples of natural products with N-alkylpyridone rings.
  • 44
    • 79955611913 scopus 로고    scopus 로고
    • For selected examples of medicinal targets with N-alkylpyridone rings
    • For selected examples of medicinal targets with N-alkylpyridone rings.
  • 60
    • 79955614166 scopus 로고    scopus 로고
    • For selected examples of Ru-catalyzed transformations
    • For selected examples of Ru-catalyzed transformations.
  • 64
    • 79955639702 scopus 로고    scopus 로고
    • For selected examples of Rh-catalyzed transformations
    • For selected examples of Rh-catalyzed transformations.
  • 67
    • 79955605232 scopus 로고    scopus 로고
    • For selected examples of Pd-catalyzed transformations, see: Notes
    • For selected examples of Pd-catalyzed transformations, see: Notes
  • 83
    • 79955614681 scopus 로고    scopus 로고
    • For details, see Electronic Supplementary Information
    • Presumably, the H originates either from the PhMe solvent or pcymeneor adventitious water. Similar results were observed when PhMe was substituted with PhH. When substrate 3a was subjected to stoichiometric amounts of [Ru(p-cymene)Cl2]2 and PPh3, product 4a was formed with complete conversion. No Ru-hydrides could beobserved by 1H NMR spectroscopy. Instead, Ru(3a) and Ru(4a) complexes were detected, suggesting that these species are catalyst resting states. For details, see Electronic Supplementary Information.
  • 86
    • 79955586723 scopus 로고    scopus 로고
    • Note
    • A Fries-type rearrangement involving formation of distinct Ruimidate and benzyltriphenylphosphonium cations via dealkylation is an alternative mechanism. Alkylation of the N atom ofalkoxypyridines is known using activated methylating agents.
  • 89
    • 79955611561 scopus 로고    scopus 로고
    • Note
    • Based on our crossover studies (Fig. 2), we favor themechanisms highlighted in Fig. 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.