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Volumn 68, Issue 17, 2003, Pages 6639-6645

A new regioselective Heck vinylation with enamides. Synthesis and investigation of fluorous-tagged bidentate ligands for fast separation

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; MICROWAVES; PALLADIUM; PHASE SEPARATION; SYNTHESIS (CHEMICAL);

EID: 0042510061     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034265i     Document Type: Article
Times cited : (86)

References (40)
  • 19
    • 0042022240 scopus 로고    scopus 로고
    • note
    • 2 and dppp monoxide in DMF. Thus, 1 equiv or (3 mol % dppp) is consumed in the generation of the active Pd(0) catalyst.
  • 21
    • 0041521313 scopus 로고    scopus 로고
    • note
    • dppp = 1,3-bis(diphenylphosphino) propane, rac-binap = racemic-2, 2′-bis(diphenylphosphino)-1,1′-binaphthyl.
  • 22
    • 0042022233 scopus 로고    scopus 로고
    • note
    • Noncomplete consumption of the vinyl triflates (1a-c) was observed after 6 h by GC/MS.
  • 23
    • 0042523136 scopus 로고    scopus 로고
    • note
    • 6 solvent retarded the reaction rate strongly.
  • 24
    • 0041521310 scopus 로고    scopus 로고
    • note
    • When monitoring the reaction mixture at 0, 15, 30, 45, and 60 min, the product 3a/homocoupling byproduct ratio increased significantly according to GC/MS.
  • 25
    • 0043024140 scopus 로고    scopus 로고
    • note
    • Employing 18.0 mol % instead of 9.0 mol % dppp at 60 °C resulted in a much slower (44 h) but equally selective internal vinylation of vinyl triflate 1a (α/β = 92/8). Unfortunately, massive homocoupling reduced the yield of product 3b (36% isolated yield).
  • 26
    • 0042022234 scopus 로고    scopus 로고
    • note
    • 2, 9 mol % dppp) with classic heating afforded lower GC/MS yields of dienamide 4 due to competing hydrogenolysis followed by aromatization and homocoupling (44% yield of 4b at 60 °C and 48% yield of 4c at 60 °C). The α/β regioselectivities were in all cases >99/1.
  • 29
    • 0042022241 scopus 로고    scopus 로고
    • note
    • 3 at room temperature furnished pure dioxide 9; see the Experimental Section.
  • 31
    • 0033533438 scopus 로고    scopus 로고
    • Compound 8b was previously reported by Francio and Leitner: Francio, G.; Leitner, W. Chem. Commun. 1999, 1663-1664.
    • (1999) Chem. Commun. , pp. 1663-1664
    • Francio, G.1    Leitner, W.2
  • 38
    • 0029565796 scopus 로고
    • Pal, K. Synthesis 1995, 12, 1485-1487.
    • (1995) Synthesis , vol.12 , pp. 1485-1487
    • Pal, K.1
  • 40
    • 0041521309 scopus 로고    scopus 로고
    • note
    • The products 4a-c were unstable and oxidized easily to the 1-hydroxy-1,2-dihydronaphthalene analogues or to the aromatic naphthalene analogues, specially 4a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.