Literature DB >> 24410210

Methylenation of perfluoroalkyl ketones using a Peterson olefination approach.

Trevor A Hamlin1, Christopher B Kelly, Robin M Cywar, Nicholas E Leadbeater.   

Abstract

An operationally simple, inexpensive, and rapid route for the olefination of a wide array of trifluoromethyl ketones to yield 3,3,3-trifluoromethylpropenes is reported. Using a Peterson olefination approach, the reaction gives good to excellent yields of the alkene products and can be performed without purification of the β-hydroxysilyl intermediate. The reaction can be extended to other perfluoroalkyl substituents and is easily scaled up. The alkenes prepared can be readily transformed into a variety of other perfluoroalkyl-containing compounds.

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Year:  2014        PMID: 24410210     DOI: 10.1021/jo402577n

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


  6 in total

1.  Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride.

Authors:  Chengbo Yao; Shuai Wang; Jack Norton; Matthew Hammond
Journal:  J Am Chem Soc       Date:  2020-01-24       Impact factor: 15.419

2.  A useful methoxyvinyl cation equivalent: α-t-butyldimethylsilyl-α-methoxyacetaldehyde.

Authors:  Christopher D McCune; Matthew L Beio; Jacob A Friest; Sandeep Ginotra; David B Berkowitz
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.

Authors:  James P Phelan; Rebecca J Wiles; Simon B Lang; Christopher B Kelly; Gary A Molander
Journal:  Chem Sci       Date:  2018-02-22       Impact factor: 9.825

4.  Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes.

Authors:  Suppachai Krajangsri; Haibo Wu; Jianguo Liu; Wangchuk Rabten; Thishana Singh; Pher G Andersson
Journal:  Chem Sci       Date:  2019-02-04       Impact factor: 9.825

5.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

6.  Nucleophilic Substitution in Solution: Activation Strain Analysis of Weak and Strong Solvent Effects.

Authors:  Trevor A Hamlin; Bas van Beek; Lando P Wolters; F Matthias Bickelhaupt
Journal:  Chemistry       Date:  2018-03-24       Impact factor: 5.236

  6 in total

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