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Volumn 125, Issue 42, 2003, Pages 12700-12701

Cine-Substitution in the Stille Coupling: Evidence for the Carbenoid Reactivity of sp3-gem-Organodimetallic Iodopalladio-trialkylstannylalkane Intermediates

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CARBENOID; CYCLOPROPANE; IODOPALLADIOSTANNYL DERIVATIVE; NORBORNENE DERIVATIVE; ORGANOTIN COMPOUND; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 0142104247     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037409j     Document Type: Article
Times cited : (73)

References (36)
  • 22
    • 0142114517 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy using mesitylene or 1,4-dioxane as an internal standard.
  • 24
    • 4544328336 scopus 로고
    • Cinnamyl methyl ether did not provide the corresponding cyclopropane, and styrene yielded cyclopropylbenzene in 5% yield. Coordination of the olefin with the Pd center has been reported to be essential in the cyclopropanation reaction by Pd-carbenes and the efficiency of the reaction greatly affected by sterics, see: Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695-702.
    • (1980) J. Org. Chem. , vol.45 , pp. 695-702
    • Anciaux, A.J.1    Hubert, A.J.2    Noels, A.F.3    Petiniot, N.4    Teyssié, P.5
  • 25
    • 0000094630 scopus 로고
    • and the Supporting Information
    • 2O, and iodostannatrane (7) with subsequent appearance of styrene, in up to 38% yield. Such rearrangement of palladium(II) complexes has been previously reported, see: Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576-8581 and the Supporting Information.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8576-8581
    • Morita, D.K.1    Stille, J.K.2    Norton, J.R.3
  • 27
    • 0142051219 scopus 로고    scopus 로고
    • note
    • 3.
  • 28
    • 0142083061 scopus 로고    scopus 로고
    • note
    • In some run, the dehalogenated byproduct, methylstannatrane, was detected.
  • 29
    • 0142083059 scopus 로고    scopus 로고
    • note
    • 2O, and propene as reported by McCrindle, see ref 20.
  • 31
    • 0142083056 scopus 로고    scopus 로고
    • note
    • 2.
  • 32
    • 0142083060 scopus 로고    scopus 로고
    • note
    • 2 trapping.
  • 36
    • 0142083057 scopus 로고    scopus 로고
    • note
    • 3Sn that is a direct reflection of its superior transmetallating ability; the carbene products were cleanly formed, and no or trace of dehalogenated byproduct was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.