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Volumn 18, Issue 17, 2012, Pages 5160-5164

CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions

Author keywords

C H activation; CDC reaction; DDQ; hydroxycoumarins; Mannich reaction; metal free reaction

Indexed keywords

C-H ACTIVATION; CDC REACTION; DDQ; HYDROXYCOUMARINS; MANNICH REACTIONS; METAL-FREE REACTION;

EID: 84859920795     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200100     Document Type: Article
Times cited : (150)

References (56)
  • 35
    • 0032482080 scopus 로고    scopus 로고
    • references therein
    • Angew. Chem. Int. Ed. 1998, 37, 1044 and references therein.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1044
  • 44
    • 0003511310 scopus 로고
    • The regioselectivity obtained in this reaction can be explained on the basis of predictions of Mannich reactions with unsymmetrical ketones, see:, H. O. House, Modern Synthetic Methods, 2 nd ed., W. A. Benjamin Inc., Berlin, 1972, p. 657. Additionally, Klussmann (ref. [10b]) and Huang (ref. [10f]) in their work on CDC reactions reported the sensitivity of Mannich reaction towards steric hindrance. Hence, the coupling generally occurs at the α carbon, which is unsubstituted in the case of unsymmetrical ketones. We believe that the regioselectivity observed in DDQ-catalyzed Mannich reaction also is due to steric hindrance. Therefore, the coupling always takes place at less-substituted side of the unsymmetrical ketones.
    • (1972) Modern Synthetic Methods , pp. 657
    • House, H.O.1
  • 54
    • 84855447048 scopus 로고    scopus 로고
    • While preparing this manuscript, a DDQ-mediated α-phosphonation of THIQ appeared, which used a stoichiometric amount of DDQ (1.1 equiv) and excess of dialkyl-H-phosphonates (2 equiv), see:, H. Wang, X. Li, F. Wu, B. Wan, Tetrahedron Lett. 2012, 53, 681.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 681
    • Wang, H.1    Li, X.2    Wu, F.3    Wan, B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.