Radical-mediated silyl- and germyldesulfonylation of vinyl and (α-fluoro)vinyl sulfones: Application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings

Organic Letters

Volumn 6, Issue 12, 2004, Pages 2047-2049

  Wnuk, Stanislaw F ^a   Garcia Jr , Pedro I ^a   Wang, Zhizhong ^a  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; GERMANIUM DERIVATIVE; HALIDE; PALLADIUM; SILANE DERIVATIVE; SULFONE DERIVATIVE; VINYL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; OXIDATION;

EID: 3042828436     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049312n     Document Type: Article

References (43)

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34. 4c
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40. (a) The (α-fluoro)vinylstannanes in combination with CuI are substrates for Stille coupling: Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-I.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476. (b) Coupling of (α-fluoro)vinylsilane 9a with iodobenzene gave variable yields of 20a (10-50%) in addition to the Z-β-fluorostyrene byproduct (30-70%). (c) CsF-assisted coupling of (1-fluorovinyl)metnyldiphenylsilane has been reported: Hanamoto, T.; Kobayashi, T. J. Org. Chem. 2003, 68, 6354.
41. (a) The (α-fluoro)vinylstannanes in combination with CuI are substrates for Stille coupling: Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-I.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476. (b) Coupling of (α-fluoro)vinylsilane 9a with iodobenzene gave variable yields of 20a (10-50%) in addition to the Z-β-fluorostyrene byproduct (30-70%). (c) CsF-assisted coupling of (1-fluorovinyl)metnyldiphenylsilane has been reported: Hanamoto, T.; Kobayashi, T. J. Org. Chem. 2003, 68, 6354.
42. (a) The (α-fluoro)vinylstannanes in combination with CuI are substrates for Stille coupling: Chen, C.; Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-I.; McCarthy, J. R. J. Org. Chem. 1999, 64, 3476. (b) Coupling of (α-fluoro)vinylsilane 9a with iodobenzene gave variable yields of 20a (10-50%) in addition to the Z-β-fluorostyrene byproduct (30-70%). (c) CsF-assisted coupling of (1-fluorovinyl)metnyldiphenylsilane has been reported: Hanamoto, T.; Kobayashi, T. J. Org. Chem. 2003, 68, 6354.
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