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Volumn 45, Issue 4, 2006, Pages 629-633

A copper(II)-catalyzed aza-friedel-crafts reaction of N-(2-Pyridyl)sulfonyl aldimines: Synthesis of unsymmetrical diaryl amines and triaryl methanes

Author keywords

Amines; Copper; Homogeneous catalysis; Nitrogen heterocycles; Schiff bases

Indexed keywords

ALDIMINES; HOMOGENEOUS CATALYSIS; NITROGEN HETEROCYCLES; SCHIFF BASES;

EID: 31044438051     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503305     Document Type: Article
Times cited : (219)

References (76)
  • 1
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    • McGraw-Hill, New York
    • For reviews on Friedel-Crafts reaction, see: a) Organic Synthesis (Ed.: M.B. Smith), McGraw-Hill, New York, 1994, p. 1313;
    • (1994) Organic Synthesis , pp. 1313
    • Smith, M.B.1
  • 2
    • 0000405865 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • b) H. Heaney in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 733;
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 733
    • Heaney, H.1
  • 7
    • 4644355914 scopus 로고    scopus 로고
    • [7b] and the asymmetric organocatalytic addition of 2-methoxyfuran to aryl aldimines (D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804) are the only examples of the participation of nonactivated imines in the AFCR.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11804
    • Uraguchi, D.1    Sorimachi, K.2    Terada, M.3
  • 40
  • 56
    • 15944408065 scopus 로고    scopus 로고
    • The only two general methods for the preparation of unsymmetrical triaryl methanes involve the condensation of unsymmetrical diaryl carbinols with electron-rich arenes under strongly acidic conditions or the displacement of the benzotriazole moiety in (benzotriazol-1-yl)diaryl methanes by p-(N,N-dimethylamino)phenylmagnesium bromide or by electron-rich arenes. See: a) S. K. Das, Shagufta, G. Panda, Tetrahedron Lett. 2005, 46, 3097;
    • (2005) Tetrahedron Lett. , vol.46 , pp. 3097
    • Das, S.K.1    Shagufta2    Panda, G.3
  • 65
    • 0037047528 scopus 로고    scopus 로고
    • For the condensation of N-tosyl aryl aldimines with a 3-lithioindole derivative, see: J. H. Wynne, W. M. Stalick, J. Org. Chem. 2002, 67, 5850.
    • (2002) J. Org. Chem. , vol.67 , pp. 5850
    • Wynne, J.H.1    Stalick, W.M.2
  • 66
    • 31044436010 scopus 로고    scopus 로고
    • note
    • No reaction between 1a and N-methylindole was observed in the absence of the Lewis acid.
  • 67
    • 31044437916 scopus 로고    scopus 로고
    • note
    • 2 becomes much slower (2 h instead of 5 min). Unfortunately, the reaction of 1a or 1e in the presence of enantiomerically pure (R)-binap, under different reaction conditions, led to virtually racemic products 2a and 2e, respectively (< 10% ee).
  • 68
    • 31044447764 scopus 로고    scopus 로고
    • note
    • 4).
  • 69
    • 13444263562 scopus 로고    scopus 로고
    • For other successful applications of the (2-pyridyl)sulfonyl group in transition-metal-catalyzed reactions, see: a) R. Gómez Arrayás, S. Cabrera, J. C. Carretero, Org. Lett. 2005, 7, 219;
    • (2005) Org. Lett. , vol.7 , pp. 219
    • Gómez Arrayás, R.1    Cabrera, S.2    Carretero, J.C.3
  • 74
    • 31044443436 scopus 로고    scopus 로고
    • note
    • 2.
  • 76
    • 31044443989 scopus 로고    scopus 로고
    • note
    • We have found only two examples of the synthesis of unsymmetrical triaryl methanes that combine both electron-rich and electron-poor aromatic rings, see references [17a, 17d].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.