Literature DB >> 20161068

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

Pablo R Sacasa1, Jessica Zayas, Stanislaw F Wnuk.   

Abstract

Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.

Entities:  

Year:  2009        PMID： 20161068      PMCID： PMC2748331          DOI： 10.1016/j.tetlet.2009.07.063

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  15 in total

1.  Organosulfur compounds: electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions.

Authors:  Srinivas Reddy Dubbaka; Pierre Vogel
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-02       Impact factor: 15.336

2.  New approach for size- and shape-controlled preparation of Pd nanoparticles with organic ligands. Synthesis and application in catalysis.

Authors:  Valentine P Ananikov; Nikolay V Orlov; Irina P Beletskaya; Victor N Khrustalev; Mikhail Yu Antipin; Tatiana V Timofeeva
Journal:  J Am Chem Soc       Date:  2007-05-19       Impact factor: 15.419

3.  Nucleic acid related compounds. 84. Synthesis of 6'-(E and Z)-halohomovinyl derivatives of adenosine, inactivation of S-adenosyl-L-homocysteine hydrolase, and correlation of anticancer and antiviral potencies with enzyme inhibition.

Authors:  S F Wnuk; C S Yuan; R T Borchardt; J Balzarini; E De Clercq; M J Robins
Journal:  J Med Chem       Date:  1994-10-14       Impact factor: 7.446

4.  Comparison of some carcinogenic, mutagenic, and biochemical properties of S-vinylhomocysteine and ethionine.

Authors:  W R Leopold; J A Miller; E C Miller
Journal:  Cancer Res       Date:  1982-11       Impact factor: 12.701

Review 5.  Vinyl sulfones: synthetic preparations and medicinal chemistry applications.

Authors:  D Christopher Meadows; Jacquelyn Gervay-Hague
Journal:  Med Res Rev       Date:  2006-11       Impact factor: 12.944

6.  Vinyl sulfonium as novel proteolytic enzyme inhibitor.

Authors:  G Zhao; Z S Zhou
Journal:  Bioorg Med Chem Lett       Date:  2001-09-03       Impact factor: 2.823

7.  Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins.

Authors:  Chen Chen; Keith Wilcoxen; Yun-Fei Zhu; James R. McCarthy
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

8.  Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones.

Authors:  Xian Huang; Dehui Duan; Weixin Zheng
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

9.  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.

Authors:  Stanislaw F Wnuk; Pedro I Garcia; Zhizhong Wang
Journal:  Org Lett       Date:  2004-06-10       Impact factor: 6.005

10.  Suicide inactivation of thioether S-methyltransferase by ethyl sulfide.

Authors:  D R Warner; J L Hoffman
Journal:  Biochemistry       Date:  1996-04-09       Impact factor: 3.162
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  3 in total

1.  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

2.  Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.

Authors:  Davide Bello; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2015-10-14       Impact factor: 2.883

3.  Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions.

Authors:  Laura Castoldi; Ester Maria Di Tommaso; Marcus Reitti; Barbara Gräfen; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-15       Impact factor: 15.336
  3 in total

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