메뉴 건너뛰기




Volumn 38, Issue 38, 1997, Pages 6617-6620

Regiospecific synthesis of unsymmetrical 2,3-Diarylquinones via stepwise Pd(O)-Catalyzed couplings of arylstannanes to doubly activated quinone equivalents

Author keywords

[No Author keywords available]

Indexed keywords

QUINONE DERIVATIVE;

EID: 0030755318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01532-3     Document Type: Article
Times cited : (23)

References (22)
  • 1
    • 0000392051 scopus 로고
    • For a powerful alternative strategy based on the use of stannylquinones, see
    • For a powerful alternative strategy based on the use of stannylquinones, see: Liebeskind, L.S.; Riesinger, S.W. J. Org. Chem. 1993, 58(2), 408-413.
    • (1993) J. Org. Chem. , vol.58 , Issue.2 , pp. 408-413
    • Liebeskind, L.S.1    Riesinger, S.W.2
  • 2
  • 4
    • 0006179060 scopus 로고    scopus 로고
    • During the preparation of this manuscript, the palladium(0)-catalyzed coupling of naphthoquinone triflates with stannanes was reported, see
    • During the preparation of this manuscript, the palladium(0)-catalyzed coupling of naphthoquinone triflates with stannanes was reported, see: Echavarren, A.M.; de Frutos, O.; Tamayo, N.; Noheda, P.; Calle, P. J. Org. Chem. 1997, 62(13), 4524-4527.
    • (1997) J. Org. Chem. , vol.62 , Issue.13 , pp. 4524-4527
    • Echavarren, A.M.1    De Frutos, O.2    Tamayo, N.3    Noheda, P.4    Calle, P.5
  • 6
    • 0030552733 scopus 로고    scopus 로고
    • Stepwise palladium-catalyzed couplings have been reported using symmetrical dibromoquinones, see
    • Stepwise palladium-catalyzed couplings have been reported using symmetrical dibromoquinones, see: Yoshida, S.; Kubo, H.; Saki, T.; Katsumura, S. Chem. Lett. 1996, 139-140.
    • (1996) Chem. Lett. , pp. 139-140
    • Yoshida, S.1    Kubo, H.2    Saki, T.3    Katsumura, S.4
  • 9
    • 0342294582 scopus 로고    scopus 로고
    • 3): 3.93 (s, 3H); 7.00 (d, J = 8.3 Hz, 2H); 7.51 (d, J = 8.8 Hz, 2H); 7.57 (s, 1H), 7.72-7.82 (m, 2H); 8.14 (d, J = 7.81 Hz, 1H); 8.19 (d, J = 7.33 Hz, 1H); 3b mp=172-173°C
    • 3): 3.93 (s, 3H); 7.00 (d, J = 8.3 Hz, 2H); 7.51 (d, J = 8.8 Hz, 2H); 7.57 (s, 1H), 7.72-7.82 (m, 2H); 8.14 (d, J = 7.81 Hz, 1H); 8.19 (d, J = 7.33 Hz, 1H); 3b mp=172-173°C.
  • 11
    • 0029979566 scopus 로고    scopus 로고
    • For leading references on the "copper-effect" in palladium-catalyzed cross-coupling reactions, see
    • For leading references on the "copper-effect" in palladium-catalyzed cross-coupling reactions, see: Allred, G.D.; Liebeskind, L.S. J. Am. Chem. Soc. 1996, 118(11), 2748-2749.
    • (1996) J. Am. Chem. Soc. , vol.118 , Issue.11 , pp. 2748-2749
    • Allred, G.D.1    Liebeskind, L.S.2
  • 13
    • 0343164242 scopus 로고    scopus 로고
    • 3): 3.89 (s, 3H); 7.02 (d, J = 8.8 Hz, 2H); 7.39 (d, J = 8.8 Hz, 2H); 7.83-7.86 (m, 2H); 8.18-8.26 (m, 2H); 4b mp = 160-162
    • 3): 3.89 (s, 3H); 7.02 (d, J = 8.8 Hz, 2H); 7.39 (d, J = 8.8 Hz, 2H); 7.83-7.86 (m, 2H); 8.18-8.26 (m, 2H); 4b mp = 160-162.
  • 14
    • 0342729615 scopus 로고    scopus 로고
    • The assignment of the major products as 1,4-naphthoquinone triflates was confirmed by the preparation of known, symmetrical 2,3-diaryl-1,4-naphthoquinones 5 and 9 from 4a and 4b, respectively
    • The assignment of the major products as 1,4-naphthoquinone triflates was confirmed by the preparation of known, symmetrical 2,3-diaryl-1,4-naphthoquinones 5 and 9 from 4a and 4b, respectively.
  • 15
    • 33751386638 scopus 로고
    • The omission of the LiCl cocatalyst led to the formation of 3-methyl-2-p-anisyl-1,4-naphthoquinone as the major product by methyl transfer from the tin reagent. For leading references on the "lithium chloride effect" in palladium-catalyzed cross-couplings, see
    • The omission of the LiCl cocatalyst led to the formation of 3-methyl-2-p-anisyl-1,4-naphthoquinone as the major product by methyl transfer from the tin reagent. For leading references on the "lithium chloride effect" in palladium-catalyzed cross-couplings, see: Farina, V.; Krishnan, B.; Marshall, D.R.; Roth, G.P. J. Org. Chem. 1993, 58(20), 5434-5444.
    • (1993) J. Org. Chem. , vol.58 , Issue.20 , pp. 5434-5444
    • Farina, V.1    Krishnan, B.2    Marshall, D.R.3    Roth, G.P.4
  • 17
    • 0342729614 scopus 로고    scopus 로고
    • 3): 3.67 (s, 3H); 3.75 (s, 3H); 6.73 (d, J = 8.8 Hz, 2H); 6.84 (d, J = 7.82 Hz, 2H); 7.04 (d, J = 8.8 Hz, 2H); 7.24 (d, J = 7.82 Hz, 2H); 7.75-7.78 (m, 2H); 8.15-8.18 (m, 2H); 8 mp=140-142°C
    • 3): 3.67 (s, 3H); 3.75 (s, 3H); 6.73 (d, J = 8.8 Hz, 2H); 6.84 (d, J = 7.82 Hz, 2H); 7.04 (d, J = 8.8 Hz, 2H); 7.24 (d, J = 7.82 Hz, 2H); 7.75-7.78 (m, 2H); 8.15-8.18 (m, 2H); 8 mp=140-142°C.
  • 22


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.