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Volumn 10, Issue 21, 2008, Pages 4887-4889

Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; INDOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; OXINDOLE; PALLADIUM;

EID: 58149159592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801844w     Document Type: Article
Times cited : (53)

References (38)
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    • For recent examples of the synthesis of 3-alkylideneoxindoles with catalysis of transition metals, see: a
    • For recent examples of the synthesis of 3-alkylideneoxindoles with catalysis of transition metals, see: (a) Kamijo, S.; Sasaki, Y.; Kanazawa, C.; Schüßeler, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 7718.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 7718
    • Kamijo, S.1    Sasaki, Y.2    Kanazawa, C.3    Schüßeler, T.4    Yamamoto, Y.5
  • 21
    • 60949105131 scopus 로고    scopus 로고
    • 1H NMR. The Z configuration of the exocyclic double bond of 3aa was assigned by an NOE study.
    • 1H NMR. The Z configuration of the exocyclic double bond of 3aa was assigned by an NOE study.
  • 22
    • 60949112904 scopus 로고    scopus 로고
    • Diederich, F, de Meijere, A, Eds, Wiley-VCH: New York, Chapter 2
    • (a) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reaction; Diederich, F., de Meijere, A., Eds.; Wiley-VCH: New York, 2004; Chapter 2.
    • (2004) Metal-Catalyzed Cross-Coupling Reaction
    • Miyaura, N.1
  • 24
    • 0037715338 scopus 로고    scopus 로고
    • For a Pd(II)-catalyzed addition reaction of arylboronic acids, see; (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
    • For a Pd(II)-catalyzed addition reaction of arylboronic acids, see; (a) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
  • 26
    • 34547194244 scopus 로고    scopus 로고
    • For a Pd(II)-catalyzed cyclization reaction of alkynones with arylboronic acids, see: (a) Song, J.; Shen, Q.; Xu, F.; Lu, X. Org. Lett. 2007, 9, 2947.
    • For a Pd(II)-catalyzed cyclization reaction of alkynones with arylboronic acids, see: (a) Song, J.; Shen, Q.; Xu, F.; Lu, X. Org. Lett. 2007, 9, 2947.
  • 30
    • 0001918453 scopus 로고    scopus 로고
    • At this time, it is not possible to rale out a mechanism involving sequential carbopalladation steps, initially operating on the alkyne moiety and next on the isocyanate moiety in a stepwise manner. For oxidative addition of arylboronic acids to Pd(O, see: (a) Cho, C. S, Uemura, S. J. Organomet. Chem. 1994, 465, 85
    • At this time, it is not possible to rale out a mechanism involving sequential carbopalladation steps, initially operating on the alkyne moiety and next on the isocyanate moiety in a stepwise manner. For oxidative addition of arylboronic acids to Pd(O), see: (a) Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.
  • 33
    • 0000789187 scopus 로고    scopus 로고
    • For a Pd(0)-catalyzed alkynylation reaction of aryl halides with alkynylboronates or alkynylborates, see: (a) Castanet, A.-S.; Colobert, F.; Schlama, T. Org. Lett. 2000, 2, 3559.
    • For a Pd(0)-catalyzed alkynylation reaction of aryl halides with alkynylboronates or alkynylborates, see: (a) Castanet, A.-S.; Colobert, F.; Schlama, T. Org. Lett. 2000, 2, 3559.
  • 36
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    • For a review of P(2-furyl)3 as ligand, see: (b) Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
    • For a review of P(2-furyl)3 as ligand, see: (b) Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997.
  • 37
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    • 4 was less effective, and its use under the same reaction conditions gave 3a1 in 42% yield (Z/E = 56/44).
    • 4 was less effective, and its use under the same reaction conditions gave 3a1 in 42% yield (Z/E = 56/44).
  • 38
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    • As reported in ref 4a, the E/Z isomerization of alkynylated 3-alkylideneoxindoles was caused by the phosphine ligand. (17) Alkynylboronate 2m was so labile that it was handled in a glovebox.
    • As reported in ref 4a, the E/Z isomerization of alkynylated 3-alkylideneoxindoles was caused by the phosphine ligand. (17) Alkynylboronate 2m was so labile that it was handled in a glovebox.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.