Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings.

Literature DB >> 15176815

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

Stanislaw F Wnuk¹, Pedro I Garcia, Zhizhong Wang.

Abstract

[reaction: see text] Radical-mediated silyl- and germyldesulfonylations of various vinyl and (alpha-fluoro)vinyl sulfones with tris(trimethylsilyl)silane and germanium hydrides provide access to vinyl and (alpha-fluoro)vinyl silanes and germanes. Upon oxidative treatment with hydrogen peroxide in basic aqueous solution, the vinyl tris(trimethylsilyl)silanes and -germanes undergo Pd-catalyzed cross-couplings with aryl halides.

Entities: Chemical

Mesh：

Substances：

Year: 2004 PMID： 15176815 DOI： 10.1021/ol049312n

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

14 in total

1. Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.

Authors: Stanislaw F Wnuk; Pablo R Sacasa; Jorge Restrepo
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2009-05 Impact factor: 1.381

2. 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.

Authors: Jean-Philippe Pitteloud; Zun-Ting Zhang; Yong Liang; Laura Cabrera; Stanislaw F Wnuk
Journal: J Org Chem Date: 2010-11-10 Impact factor: 4.354

3. Radical-mediated thiodesulfonylation of the vinyl sulfones: Access to (α-fluoro)vinyl sulfides.

Authors: Pablo R Sacasa; Jessica Zayas; Stanislaw F Wnuk
Journal: Tetrahedron Lett Date: 2009-09-23 Impact factor: 2.415

4. Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.

Authors: Christopher D McCune; Matthew L Beio; Jill M Sturdivant; Roberto de la Salud-Bea; Brendan M Darnell; David B Berkowitz
Journal: J Am Chem Soc Date: 2017-09-28 Impact factor: 15.419

10. Hydrogermylation of 5-ethynyluracil nucleosides: formation of 5-(2-germylvinyl)uracil and 5-(2-germylacetyl)uracil nucleosides.

Authors: Yong Liang; Jean-Philippe Pitteloud; Stanislaw F Wnuk
Journal: J Org Chem Date: 2013-05-13 Impact factor: 4.354

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

1. Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.

3. Radical-mediated thiodesulfonylation of the vinyl sulfones: Access to (α-fluoro)vinyl sulfides.

4. Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.

5. Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones.

6. Arylchlorogermanes/TBAF/"moist" toluene: a promising combination for Pd-catalyzed Germyl-Stille cross-coupling.

7. Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.

8. Vinyl Tris(trimethylsilyl)silanes: Substrates for Hiyama Coupling.

9. S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit.

10. Hydrogermylation of 5-ethynyluracil nucleosides: formation of 5-(2-germylvinyl)uracil and 5-(2-germylacetyl)uracil nucleosides.