Literature DB >> 16930033

Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones.

Chuanfa Ni1, Ya Li, Jinbo Hu.   

Abstract

The unprecedented nucleophilic fluoroalkylation of simple epoxides with fluorinated sulfones was achieved to give the beta-fluoroalkyl alcohols in one step. The negative "fluorine effect" in the nucleophilic fluoroalkylation of epoxides with fluorinated carbanions was probed by the reactivity comparison between carbanions PhSO2CF2- (3) and PhSO2CCl2- (4) and between carbanions PhSO2CHF- (7) and PhSO2CHCl- (13). The mediation of this fluorine effect by introducing another electron-withdrawing benzenesulfonyl group was found to be an effective way to significantly increase the nucleophilicity of the fluorinated carbanions, with the reactivity order [(PhSO2)2CF-] (16) > PhSO2CFH- (7) >> PhSO2CF2- (3).

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Year:  2006        PMID： 16930033     DOI： 10.1021/jo060955l

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


  8 in total

1.  Alpha-fluoro-alpha-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: efficient stereoselective Michael addition to chalcones.

Authors:  G K Surya Prakash; Fang Wang; Timothy Stewart; Thomas Mathew; George A Olah
Journal:  Proc Natl Acad Sci U S A       Date:  2009-02-23       Impact factor: 11.205

2.  2-(1,3-Benzoxazol-2-ylsulfan-yl)-1-phenyl-ethanone.

Authors:  Hossein Loghmani-Khouzani; Dariush Hajiheidari; Ward T Robinson; Noorsaadah Abdul Rahman; Reza Kia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-29

3.  2-(Benzo[d]thia-zol-2-ylsulfon-yl)-1-(4-bromo-phen-yl)ethanone.

Authors:  Hossein Loghmani-Khouzani; Dariush Hajiheidari; Ward T Robinson; Reza Kia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-19

4.  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

5.  2-(1,3-Benzothia-zol-2-ylsulfan-yl)-1-phenyl-ethanone.

Authors:  Hossein Loghmani-Khouzani; Dariush Hajiheidari; Ward T Robinson; Noorsaadah Abdul Rahman; Reza Kia
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-12

Review 6.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

7.  Efficient 1,4-addition of alpha-substituted fluoro(phenylsulfonyl)methane derivatives to alpha,beta-unsaturated compounds.

Authors:  G K Surya Prakash; Xiaoming Zhao; Sujith Chacko; Fang Wang; Habiba Vaghoo; George A Olah
Journal:  Beilstein J Org Chem       Date:  2008-05-21       Impact factor: 2.883

8.  Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H reagents catalyzed by chiral quaternary ammonium salts.

Authors:  Chuanfa Ni; Fang Wang; Jinbo Hu
Journal:  Beilstein J Org Chem       Date:  2008-06-26       Impact factor: 2.883
  8 in total

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