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Literature DB >> 23397884

Late-stage deoxyfluorination of alcohols with PhenoFluor.

Filippo Sladojevich¹, Sophie I Arlow, Pingping Tang, Tobias Ritter.

Abstract

An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.

Entities: Chemical

Mesh：

Substances：

Year: 2013 PMID： 23397884 PMCID： PMC3596866 DOI： 10.1021/ja3125405

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

27 in total

1. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

Authors: Chad A Lewis; Scott J Miller
Journal: Angew Chem Int Ed Engl Date: 2006-08-25 Impact factor: 15.336

2. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Authors: Peter A Jordan; Scott J Miller
Journal: Angew Chem Int Ed Engl Date: 2012-02-08 Impact factor: 15.336

3. Deoxyfluorination of phenols.

Authors: Pingping Tang; Weike Wang; Tobias Ritter
Journal: J Am Chem Soc Date: 2011-07-12 Impact factor: 15.419

4. Derivatives of 6-aminopenicillanic acid. XI. Alpha-amino-p-hydroxybenzylpenicillin.

Authors: A A Long; J H Nayler; H Smith; T Taylor; N Ward
Journal: J Chem Soc Perkin 1 Date: 1971

5. Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity.

Authors: Teruo Umemoto; Rajendra P Singh; Yong Xu; Norimichi Saito
Journal: J Am Chem Soc Date: 2010-12-02 Impact factor: 15.419

6. Site-selective bromination of vancomycin.

Authors: Tejas P Pathak; Scott J Miller
Journal: J Am Chem Soc Date: 2012-03-30 Impact factor: 15.419

7. A new reagent for direct difluoromethylation.

Authors: Yuta Fujiwara; Janice A Dixon; Rodrigo A Rodriguez; Ryan D Baxter; Darryl D Dixon; Michael R Collins; Donna G Blackmond; Phil S Baran
Journal: J Am Chem Soc Date: 2012-01-13 Impact factor: 15.419

8. Silver-catalyzed late-stage fluorination.

Authors: Pingping Tang; Takeru Furuya; Tobias Ritter
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

Review 9. Carbon-fluorine bond formation.

Authors: Takeru Furuya; Christian A Kuttruff; Tobias Ritter
Journal: Curr Opin Drug Discov Devel Date: 2008-11

10. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

Authors: Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal: J Am Chem Soc Date: 2013-11-12 Impact factor: 15.419

Late-stage deoxyfluorination of alcohols with PhenoFluor.

1. Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

2. An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

3. Deoxyfluorination of phenols.

4. Derivatives of 6-aminopenicillanic acid. XI. Alpha-amino-p-hydroxybenzylpenicillin.

5. Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity.

6. Site-selective bromination of vancomycin.

7. A new reagent for direct difluoromethylation.

8. Silver-catalyzed late-stage fluorination.

Review 9. Carbon-fluorine bond formation.

10. Guided desaturation of unactivated aliphatics.

1. Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Review 2. Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

3. AlkylFluor: Deoxyfluorination of Alcohols.

4. Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

5. Alkyl Aryl Ether Bond Formation with PhenoFluor.

6. Palladium(III)-catalyzed fluorination of arylboronic acid derivatives.

7. Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

8. SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

9. Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

10. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.