Literature DB >> 18841918

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

Maria del Solar1, Arun K Ghosh, Barbara Zajc.   

Abstract

Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl alpha-(1,3-benzothiazol-2-ylsulfanyl)-alpha-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile in the presence of DBU leading to alpha-fluoro acrylonitriles in high yields and with good Z-stereoselectivity. Lowering of reaction temperature increases the Z selectivity.

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Year:  2008        PMID： 18841918      PMCID： PMC2771215          DOI： 10.1021/jo801235x

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 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.  The smiles rearrangement and the julia-kocienski olefination reaction.

Authors:  Krzysztof Plesniak; Andrzej Zarecki; Jerzy Wicha
Journal:  Top Curr Chem       Date:  2007

3.  Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins.

Authors:  Jérôme Waser; Boris Gaspar; Hisanori Nambu; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

4.  High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations.

Authors:  Arun K Ghosh; Barbara Zajc
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

5.  Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase.

Authors:  Joseph P Burkhart; Philip M Weintraub; Cynthia A Gates; Robert J Resvick; Roy J Vaz; Dirk Friedrich; Michael R Angelastro; Philippe Bey; Norton P Peet
Journal:  Bioorg Med Chem       Date:  2002-04       Impact factor: 3.641

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

Authors:  Maggie He; Arun K Ghosh; Barbara Zajc
Journal:  Synlett       Date:  2008-04-01       Impact factor: 2.454

7.  Efficient synthesis of 2-modified 1alpha,25-dihydroxy-19-norvitamin D3 with Julia olefination: high potency in induction of differentiation on HL-60 cells.

Authors:  Keiichiro Ono; Akihiro Yoshida; Nozomi Saito; Toshie Fujishima; Shinobu Honzawa; Yoshitomo Suhara; Seishi Kishimoto; Takayuki Sugiura; Keizo Waku; Hiroaki Takayama; Atsushi Kittaka
Journal:  J Org Chem       Date:  2003-09-19       Impact factor: 4.354

8.  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

9.  Synthesis of 21,21-difluoro-3 beta-hydroxy-20-methylpregna-5,20-diene and 5,16,20-triene as potential inhibitors of steroid C17(20) lyase.

Authors:  Philip M Weintraub; Amy K Holland; Cynthia A Gates; William R Moore; Robert J Resvick; Philippe Bey; Norton P Peet
Journal:  Bioorg Med Chem       Date:  2003-02-06       Impact factor: 3.641

10.  Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid.

Authors:  Liang Xu; Jie Cheng; Mark L Trudell
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354
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  8 in total

1.  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

2.  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

3.  Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis.

Authors:  Arun K Ghosh; Barbara Zajc
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

4.  Stereoselective synthesis of conjugated fluoro enynes.

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

5.  Alpha-fluorovinyl Weinreb amides and alpha-fluoroenones from a common fluorinated building block.

Authors:  Arun K Ghosh; Shaibal Banerjee; Saikat Sinha; Soon Bang Kang; Barbara Zajc
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

6.  Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

Authors:  Barbara Zajc; Rakesh Kumar
Journal:  Synthesis (Stuttg)       Date:  2010       Impact factor: 3.157

7.  Tris(2-hydroxy-ethyl)ammonium 1,3-benzo-thia-zole-2-thiol-ate.

Authors:  Ji-Qin Zhu; Hua-Cai Fang; Bi-Yun Chen; Mao-Song Feng; Jing-Ning Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-20

8.  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
  8 in total

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