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Volumn 73, Issue 2, 2008, Pages 756-759

A novel palladium-catalyzed dicarbonylation process leading to coumarins

Author keywords

[No Author keywords available]

Indexed keywords

COUMARINS; DICARBONYLATION; ROOM TEMPERATURE;

EID: 40949129064     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702243m     Document Type: Article
Times cited : (54)

References (82)
  • 3
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    • Coumarins (2H-1-benzopyran-2-ones, 2H-chromen-2-ones) have been classically synthesized by several routes, such as the reaction of 2-hydroxybenzaldehydes or 2-hydroxyaryl alkyl ketones with carboxylic anhydrides [Kostanecki-Robinson reaction: (a) Kostanechi, S. v.; Rózycki, A. Ber. Dtsch. Chem. Ges. 1901, 34, 102-112.
    • (1901) Ber. Dtsch. Chem. Ges. , vol.34 , pp. 102-112
    • Kostanechi, S.V.1    Rózycki, A.2
  • 6
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    • (d) Shah, D. N.; Shah, N. M. J. Am. Chem. Soc. 1955, 77, 1699-1700] and the reaction of β-keto esters with phenols [von Pechmann reaction
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 1699-1700
    • Shah, D.N.1    Shah, N.M.2
  • 9
    • 0007063662 scopus 로고
    • Wiley: New York
    • (g) Horning, E. C. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, pp 281-285]. Other classical coumarins syntheses include the Perkin
    • (1955) Organic Syntheses , vol.3 , pp. 281-285
    • Horning, E.C.1
  • 10
    • 0000989392 scopus 로고
    • Knoevenagel
    • (h) Johnson, J. R. Org. React. 1942, 1, 210-265], Knoevenagel
    • (1942) Org. React. , vol.1 , pp. 210-265
    • Johnson, J.R.1
  • 11
    • 0000248247 scopus 로고
    • (i) Jones, G. Org. React. 1967, 15, 204-599.
    • (1967) Org. React. , vol.15 , pp. 204-599
    • Jones, G.1
  • 15
    • 84855209169 scopus 로고
    • Wittig
    • (m) Fürstner, A. Synthesis 1989, 571-590], and Wittig
    • (1989) Synthesis , pp. 571-590
    • Fürstner, A.1
  • 25
    • 34547957084 scopus 로고    scopus 로고
    • For some very recent developments in the synthesis of coumarins, see: (a) Henry, C. E.; Kwon, O. Org. Lett. 2007, 9, 3069-3072.
    • (2007) Org. Lett. , vol.9 , pp. 3069-3072
    • Henry, C.E.1    Kwon, O.2
  • 37
    • 0037448880 scopus 로고    scopus 로고
    • Only a few transition metal-catalyzed approaches to the synthesis of coumarins have been reported. For representative examples, see ref 9 and: (a) Trost, B. M.; Toste, F. D.; Greenman, K. J. Am. Chem. Soc. 2003, 125, 4518-4526.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4518-4526
    • Trost, B.M.1    Toste, F.D.2    Greenman, K.3
  • 42
    • 29244433159 scopus 로고    scopus 로고
    • To our knowledge, only very few reports on coumarin synthesis by a direct carbonylation approach have appeared in the literature so far: (a) Cao, H.; Xiao, W. J. Can. J. Chem. 2005, 83, 826-831.
    • (2005) Can. J. Chem. , vol.83 , pp. 826-831
    • Cao, H.1    Xiao, W.J.2
  • 45
    • 0028015780 scopus 로고
    • None of these methods, however, led to 3-[(alkoxycarbonyl)methyl] coumarins by direct dicarbonylation of acyclic substrates
    • (d) Catellani, M.; Chiusoli, G. P.; Fagnola, M. C.; Solari, G. Tetrahedron Lett. 1994, 35, 5923-5926. None of these methods, however, led to 3-[(alkoxycarbonyl)methyl]coumarins by direct dicarbonylation of acyclic substrates.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5923-5926
    • Catellani, M.1    Chiusoli, G.P.2    Fagnola, M.C.3    Solari, G.4
  • 66
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    • (b) Sekar, N. Colourage 2003, 50, 55-56.
    • (2003) Colourage , vol.50 , pp. 55-56
    • Sekar, N.1
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    • (c) Maeda, M. Laser Dyes; Academic Press: New York, 1984.
    • (1984) Laser Dyes
    • Maeda, M.1
  • 80
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    • Cyclocarbonylation
    • Negishi, E., Ed.; Wiley-Interscience: New York
    • For a recent monograph on Pd-catalyzed cyclocarbonylationalkoxycarbonylation reactions, including a detailed mechanistic discussion, see: Gabriele, B.; Salerno, G. Cyclocarbonylation. In: Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. II; pp 2623-2641.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 2623-2641
    • Gabriele, B.1    Salerno, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.