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Volumn 1, Issue 4, 1999, Pages 545-547

Use of the Stille coupling reaction on heteroaromatic cations: Synthesis of substituted quinolizinium salts

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EID: 0001200278     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990626y     Document Type: Article
Times cited : (34)

References (40)
  • 7
    • 0001186913 scopus 로고
    • Abel, E. W., Stone; F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, Chapter 3.4
    • (b) Farina, F. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone; F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1995; Vol. 12, Chapter 3.4, p 161.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 161
    • Farina, F.1
  • 17
    • 33845376366 scopus 로고
    • Although there are a few reports on LiCl/Pd(0)-promoted cross-coupling reactions, the salt effects have been examined with different electrophiles. (a) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3033
    • Scott, W.J.1    Stille, J.K.2
  • 23
    • 0025040237 scopus 로고
    • Homocoupling products derived from the stannane have been observed, with the homocoupling of the electrophile being less common. (a) Dubois, E.; Beau, J.-M. Tetrahedron Lett. 1990, 31, 5165.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5165
    • Dubois, E.1    Beau, J.-M.2
  • 26
    • 0042075413 scopus 로고    scopus 로고
    • Reference 6d
    • Reference 6d.
  • 31
    • 0042075414 scopus 로고    scopus 로고
    • note
    • The homocoupling product [1,1′]biquinolizinium dipicrate has been characterized (see Supporting Information).
  • 37
    • 0042576415 scopus 로고    scopus 로고
    • note
    • 4 (0.0086 mmol, 10 mg) were slowly added, and then 0.225 mmol of the corresponding stannane was added. After stirring at room temperature for 15-20 h, the solution was filtered through a small pad of Celite and washed with methanol. The solution was concentrated and the solid isolated by filtration. All compounds were isolated as picrates (TNP) by treatment of the crude bromide with a slight excess of sodium picrate in refluxing ethanol for 1 h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.