Literature DB >> 22544979

Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

Barbara Zajc1, Rakesh Kumar.   

Abstract

The Julia-Kocienski olefination provides a versatile platform for the synthesis of fluorovinyl compounds. This review describes our efforts as well as those of others in the synthesis of various fluorinated aryl and heteroaryl sulfones and their utility as olefination reagents for the modular assembly of fluoroalkenes. Where data is available, the influence of the fluorine atom on the reactivity of the olefination reagents and the stereochemical outcome of the olefination are described.

Entities:  

Year:  2010        PMID： 22544979      PMCID： PMC3337086          DOI： 10.1055/s-0029-1218789

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  31 in total

1.  Fluorinated Ylides and Related Compounds.

Authors:  Donald J. Burton; Zhen-Yu Yang; Weiming Qiu
Journal:  Chem Rev       Date:  1996-08-01       Impact factor: 60.622

2.  2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: a reagent for nucleophilic monofluoromethylation of aldehydes.

Authors:  Tatsuya Furukawa; Yosuke Goto; Jumpei Kawazoe; Etsuko Tokunaga; Shuichi Nakamura; Yudong Yang; Hongguang Du; Akikazu Kakehi; Motoo Shiro; Norio Shibata
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-22       Impact factor: 15.336

3.  Studies toward the synthesis of alpha-fluorinated phosphonates via tin-mediated cleavage of alpha-fluoro-alpha-(pyrimidin-2-ylsulfonyl)alkylphosphonates. Intramolecular cyclization of the alpha-phosphonyl radicals.

Authors:  Stanislaw F Wnuk; Luis A Bergolla; Pedro I Garcia
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

4.  A persistent alpha-fluorocarbanion and its analogues: preparation, characterization, and computational study.

Authors:  G K Surya Prakash; Fang Wang; Nan Shao; Thomas Mathew; Golam Rasul; Ralf Haiges; Timothy Stewart; George A Olah
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Modified Julia fluoroolefination: selective preparation of fluoroalkenoates.

Authors:  Emmanuel Pfund; Cyril Lebargy; Jacques Rouden; Thierry Lequeux
Journal:  J Org Chem       Date:  2007-09-19       Impact factor: 4.354

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

Authors:  Maria del Solar; Arun K Ghosh; Barbara Zajc
Journal:  J Org Chem       Date:  2008-10-08       Impact factor: 4.354

7.  Perspective on fluorocarbon chemistry.

Authors:  David M Lemal
Journal:  J Org Chem       Date:  2004-01-09       Impact factor: 4.354

8.  Direct synthesis of 8-fluoro purine nucleosides via metalation-fluorination.

Authors:  Arun K Ghosh; Pallavi Lagisetty; Barbara Zajc
Journal:  J Org Chem       Date:  2007-09-29       Impact factor: 4.354

9.  N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: a new difluoromethylation reagent for S-, N-, and C-nucleophiles.

Authors:  Wei Zhang; Fei Wang; Jinbo Hu
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

10.  Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages.

Authors:  David B Berkowitz; Kannan R Karukurichi; Roberto de la Salud-Bea; David L Nelson; Christopher D McCune
Journal:  J Fluor Chem       Date:  2008-09       Impact factor: 2.050
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  14 in total

1.  Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks.

Authors:  Wei Wei; Rama Kanwar Khangarot; Lothar Stahl; Cristina Veresmortean; Padmanava Pradhan; Lijia Yang; Barbara Zajc
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

2.  Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes1.

Authors:  Deborah O Ayeni; Samir K Mandal; Barbara Zajc
Journal:  Tetrahedron Lett       Date:  2013-11-06       Impact factor: 2.415

3.  Expedient synthesis of α-substituted fluoroethenes.

Authors:  Samir K Mandal; Arun K Ghosh; Rakesh Kumar; Barbara Zajc
Journal:  Org Biomol Chem       Date:  2012-02-20       Impact factor: 3.876

4.  Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents.

Authors:  Rakesh Kumar; Padmanava Pradhan; Barbara Zajc
Journal:  Chem Commun (Camb)       Date:  2011-02-18       Impact factor: 6.222

5.  E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents.

Authors:  Rakesh Kumar; Govindra Singh; Louis J Todaro; Lijia Yang; Barbara Zajc
Journal:  Org Biomol Chem       Date:  2015-02-07       Impact factor: 3.876

6.  Stereoselective synthesis of conjugated fluoro enynes.

Authors:  Rakesh Kumar; Barbara Zajc
Journal:  J Org Chem       Date:  2012-09-24       Impact factor: 4.354

7.  Modular synthesis of N-vinyl benzotriazoles.

Authors:  Govindra Singh; Rakesh Kumar; Jorge Swett; Barbara Zajc
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

8.  Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.

Authors:  Rui Guo; Xiaotian Qi; Hengye Xiang; Paul Geaneotes; Ruihan Wang; Peng Liu; Yi-Ming Wang
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-14       Impact factor: 15.336

9.  Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape.

Authors:  Shaibal Banerjee; Saikat Sinha; Padmanava Pradhan; Alessio Caruso; Daniel Liebowitz; Damon Parrish; Miriam Rossi; Barbara Zajc
Journal:  J Org Chem       Date:  2016-03-22       Impact factor: 4.354

10.  Synthesis of regiospecifically fluorinated conjugated dienamides.

Authors:  Mohammad Chowdhury; Samir K Mandal; Shaibal Banerjee; Barbara Zajc
Journal:  Molecules       Date:  2014-04-10       Impact factor: 4.411
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