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Volumn 12, Issue 13, 2010, Pages 2948-2950

Rhenium-catalyzed synthesis of indenones by novel dehydrative trimerization of aryl aldehydes via C-H bond activation

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; INDENE DERIVATIVE; RHENIUM;

EID: 77954121577     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100947p     Document Type: Article
Times cited : (72)

References (42)
  • 12
    • 77954092636 scopus 로고    scopus 로고
    • There have been several reports on transition-metal-catalyzed syntheses of indenone derivatives. See
    • There have been several reports on transition-metal-catalyzed syntheses of indenone derivatives. See
  • 18
    • 77954140711 scopus 로고    scopus 로고
    • Indenones are used as starting materials for synthesizing indenes and indenyl-transition-metal complexes. See
    • Indenones are used as starting materials for synthesizing indenes and indenyl-transition-metal complexes. See
  • 21
    • 14944367862 scopus 로고    scopus 로고
    • Indenones are key intermediates for the synthesis of bioactive products. See
    • Indenones are key intermediates for the synthesis of bioactive products. See: Walspurger, S.; Vasilyev, A. V.; Sommer, J.; Pale, P. Tetrahedron 2005, 61, 3559
    • (2005) Tetrahedron , vol.61 , pp. 3559
    • Walspurger, S.1    Vasilyev, A.V.2    Sommer, J.3    Pale, P.4
  • 22
    • 77954092635 scopus 로고    scopus 로고
    • 12, 0%
    • 12, 0%.
  • 23
    • 77954113156 scopus 로고    scopus 로고
    • Investigation of several additives: aniline, 80%; 4-methoxyaniline, 75%; 4-trifluoromethylaniline, 98%; N -methylaniline, 62%; N, N -dimethylaniline, 0%
    • Investigation of several additives: aniline, 80%; 4-methoxyaniline, 75%; 4-trifluoromethylaniline, 98%; N -methylaniline, 62%; N, N -dimethylaniline, 0%.
  • 24
    • 77954122467 scopus 로고    scopus 로고
    • 5 and N -phenylacetamide, an intermediate, isobenzofuran, was not observed, and benzaldehyde was recovered completely. The result indicates that the formation of the isobenzofurans from 2 equiv of aldehydes requires heating at 180 -°C
    • 5 and N -phenylacetamide, an intermediate, isobenzofuran, was not observed, and benzaldehyde was recovered completely. The result indicates that the formation of the isobenzofurans from 2 equiv of aldehydes requires heating at 180 -°C.
  • 25
    • 77954097631 scopus 로고    scopus 로고
    • In the case of known cyclotrimerizations of aldehydes, 1,3,5-trioxane derivatives are formed. See
    • In the case of known cyclotrimerizations of aldehydes, 1,3,5-trioxane derivatives are formed. See
  • 26
    • 77954102700 scopus 로고    scopus 로고
    • (Daicel Chemical Industries, Ltd.), JP P2002-145877A
    • Ishii, Y.; Nakano, T. (Daicel Chemical Industries, Ltd.), JP P2002-145877A, 2002.
    • (2002)
    • Ishii, Y.1    Nakano, T.2
  • 28
    • 77954100266 scopus 로고    scopus 로고
    • We have already reported the rhenium-catalyzed synthesis of isobenzofuran derivatives via the insertion of aldehydes into a C-H bond of aromatic compounds followed by intramolecular nucleophilic cyclization and dehydration. See ref 3d
    • We have already reported the rhenium-catalyzed synthesis of isobenzofuran derivatives via the insertion of aldehydes into a C-H bond of aromatic compounds followed by intramolecular nucleophilic cyclization and dehydration. See ref 3d.
  • 29
    • 0001723369 scopus 로고
    • There has been a report on the reaction between 1-phenylisobenzofuran and a dienophile by Diels-Alder reaction. See
    • There has been a report on the reaction between 1-phenylisobenzofuran and a dienophile by Diels-Alder reaction. See: Tobia, D.; Rickborn, B. J. Org. Chem. 1986, 51, 3849
    • (1986) J. Org. Chem. , vol.51 , pp. 3849
    • Tobia, D.1    Rickborn, B.2
  • 31
    • 77954124082 scopus 로고    scopus 로고
    • Another possibility is the formation of an aldimine from hydroxy amide intermediate A by the elimination of acetic acid from A, and the C-H activation of the aldimine occurs
    • Another possibility is the formation of an aldimine from hydroxy amide intermediate A by the elimination of acetic acid from A, and the C-H activation of the aldimine occurs.
  • 32
    • 77954138865 scopus 로고    scopus 로고
    • 3) atom as a directing group, see
    • 3) atom as a directing group, see
  • 37
    • 77954108181 scopus 로고    scopus 로고
    • 2) atom] is effective as a directing group
    • 2) atom] is effective as a directing group.
  • 38
    • 77954107070 scopus 로고    scopus 로고
    • There have been several reports on nucleophilic addition of isobenzofurans to electrophiles. See
    • There have been several reports on nucleophilic addition of isobenzofurans to electrophiles. See
  • 41
    • 77954112083 scopus 로고    scopus 로고
    • Instead of steps 7 and 8, the following step could also occur: hetero-Diels-Alder reaction between the formed isobenzofuran intermediate and the third aldehyde. In fact, there has been a report on a Diels-Alder reaction between an isobenzofuran derivative and aldehyde. See ref 13
    • Instead of steps 7 and 8, the following step could also occur: hetero-Diels-Alder reaction between the formed isobenzofuran intermediate and the third aldehyde. In fact, there has been a report on a Diels-Alder reaction between an isobenzofuran derivative and aldehyde. See ref 13.
  • 42
    • 77954115440 scopus 로고    scopus 로고
    • 2O, which is formed by dehydration as shown in Scheme 1, steps 6 and 11
    • 2O, which is formed by dehydration as shown in Scheme 1, steps 6 and 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.