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Volumn 75, Issue 23, 2010, Pages 8199-8212

Fluoride-promoted cross-coupling of chloro(mono-, di-, or triphenyl)germanes with aryl halides in "moist" toluene. Multiple transfer of the phenyl group from organogermane substrates and comparison of the coupling efficiencies of chloro(phenyl)germanes with their corresponding stannane and silane counterparts

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL GROUP; ARYL HALIDES; CHLORIDE LIGANDS; COUPLING EFFICIENCY; CROSS-COUPLINGS; GERMANES; NMR STUDIES; ORGANOGERMANES; PHENYL GROUP; STANNANE; TETRABUTYLAMMONIUM FLUORIDES;

EID: 78650257273     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101848f     Document Type: Article
Times cited : (34)

References (69)
  • 33
    • 78650259157 scopus 로고    scopus 로고
    • 3 was basically ineffective under various conditions. (9)
    • 3 was basically ineffective under various conditions. (9)
  • 34
    • 0013017424 scopus 로고    scopus 로고
    • d has been employed to advantage in organic synthesis. For example, doubly substituted α-germanyl-β-stannyl(or silyl or halo)alkenes undergo Pd-catalyzed couplings chemoselectively at the β carbon to afford α-germanyl-β-substituted alkenes
    • d has been employed to advantage in organic synthesis. For example, doubly substituted α-germanyl-β-stannyl(or silyl or halo)alkenes undergo Pd-catalyzed couplings chemoselectively at the β carbon to afford α-germanyl-β-substituted alkenes: Spivey, A. C.; Turner, D. J.; Turner, M. L.; Yeates, S. Org. Lett. 2002, 4, 1899-1902
    • (2002) Org. Lett. , vol.4 , pp. 1899-1902
    • Spivey, A.C.1    Turner, D.J.2    Turner, M.L.3    Yeates, S.4
  • 38
    • 42749092334 scopus 로고    scopus 로고
    • Vinyl tris(trimethylsilyl)germanes (17) and silanes (35a) undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides with comparable efficiency upon oxidative treatment with hydrogen peroxide in basic aqueous solution
    • Vinyl tris(trimethylsilyl)germanes (17) and silanes (35a) undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides with comparable efficiency upon oxidative treatment with hydrogen peroxide in basic aqueous solution: Wang, Z.; Pitteloud, J.-P.; Montes, L.; Rapp, M.; Derane, D.; Wnuk, S. F. Tetrahedron 2008, 64, 5322-5327
    • (2008) Tetrahedron , vol.64 , pp. 5322-5327
    • Wang, Z.1    Pitteloud, J.-P.2    Montes, L.3    Rapp, M.4    Derane, D.5    Wnuk, S.F.6
  • 40
    • 78650285467 scopus 로고    scopus 로고
    • Yields for the cross-coupling products 10, throughout the manuscript, are based upon the theoretical possibilities of transferring one, two, three or four phenyl groups from the organometallic precursors (6 - 8 and 12 - 21) independent of the equivalency of halides used
    • Yields for the cross-coupling products 10, throughout the manuscript, are based upon the theoretical possibilities of transferring one, two, three or four phenyl groups from the organometallic precursors (6 - 8 and 12 - 21) independent of the equivalency of halides used.
  • 41
    • 78650276839 scopus 로고    scopus 로고
    • It is noteworthy that yields of cross-coupling products 10, based on 1-iodonaphthalene as limiting reagents, would be, for instance, 49% (entry 10) and 81% (entry 11) in Table 2
    • It is noteworthy that yields of cross-coupling products 10, based on 1-iodonaphthalene as limiting reagents, would be, for instance, 49% (entry 10) and 81% (entry 11) in Table 2.
  • 45
    • 0035925228 scopus 로고    scopus 로고
    • For a review on water-accelerated organic transformations see
    • For a review on water-accelerated organic transformations see: Ribe, S.; Wipf, P. Chem. Commun. 2001, 299-307
    • (2001) Chem. Commun. , pp. 299-307
    • Ribe, S.1    Wipf, P.2
  • 50
    • 78650280110 scopus 로고    scopus 로고
    • U.S. Pat. Appl. 7,524,992 B2
    • Vastra, J.; Chimie, R U.S. Pat. Appl. 7,524,992 B2, 2009.
    • (2009)
    • Vastra, J.1    Chimie, R.2
  • 54
    • 78650268854 scopus 로고    scopus 로고
    • reported that the reactivity of the silicates critically depends on the number of fluorine atoms on the silicon. (29)
    • Hiyama et al. reported that the reactivity of the silicates critically depends on the number of fluorine atoms on the silicon. (29)
    • Hiyama1
  • 66
    • 0001231308 scopus 로고
    • Conversion of the analogous fluorosilanes with tetraethylammonium fluoride and water or hypervalent fluorosilicates with water to produce corresponding disilioxane has been reported
    • Conversion of the analogous fluorosilanes with tetraethylammonium fluoride and water or hypervalent fluorosilicates with water to produce corresponding disilioxane has been reported: Johnson, S. E.; Deiters, J. A.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1989, 111, 3250-3258
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3250-3258
    • Johnson, S.E.1    Deiters, J.A.2    Day, R.O.3    Holmes, R.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.