Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction

Barkakaty, Balaka; Talukdar, Bandana; Lokitz, Bradley

doi:10.3390/molecules200815098

Title: Addition of CFCl₃ to Aromatic Aldehydes via in Situ Grignard Reaction

Abstract

In the case of synthetic modification of trichlorofluoromethane (CFCl₃) to non-volatile and useful fluorinated precursors, we realized that it is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In our report, we present a novel method for in situ Grignard reaction using magnesium powder and CFCl₃ for synthesis of dichlorofluoromethyl aromatic alcohols.

Authors:

Barkakaty, Balaka ^[1]; Talukdar, Bandana ^[2]; Lokitz, Bradley ^[1]

Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Independent Researcher, Guwahati (India)

Publication Date:: Tue Aug 18 00:00:00 EDT 2015

Research Org.:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1265863

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: Molecules

Additional Journal Information:: Journal Volume: 20; Journal Issue: 8; Journal ID: ISSN 1420-3049

Publisher:: MDPI

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; CFCl3; magnesium; grignard reaction; in-situ process; aromatic aldehydes

Citation Formats


                    Barkakaty, Balaka, Talukdar, Bandana, and Lokitz, Bradley. Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction.  United States: N. p., 2015. 
Web.  doi:10.3390/molecules200815098.

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                    Barkakaty, Balaka, Talukdar, Bandana, & Lokitz, Bradley. Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction.  United States.  https://doi.org/10.3390/molecules200815098

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                    Barkakaty, Balaka, Talukdar, Bandana, and Lokitz, Bradley. Tue .  
"Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction".  United States.  https://doi.org/10.3390/molecules200815098.  https://www.osti.gov/servlets/purl/1265863.

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@article{osti_1265863,

  title        = {Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction},

  author       = {Barkakaty, Balaka and Talukdar, Bandana and Lokitz, Bradley},

  abstractNote = {In the case of synthetic modification of trichlorofluoromethane (CFCl3) to non-volatile and useful fluorinated precursors, we realized that it is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In our report, we present a novel method for in situ Grignard reaction using magnesium powder and CFCl3 for synthesis of dichlorofluoromethyl aromatic alcohols.},

  doi          = {10.3390/molecules200815098},

  journal      = {Molecules},

  number       = 8,

  volume       = 20,

  place        = {United States},

  year         = {Tue Aug 18 00:00:00 EDT 2015},

  month        = {Tue Aug 18 00:00:00 EDT 2015}

}

Copy to clipboard

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Fluorochloro-, fluorobromo-, and monofluorocarbene generation via organolithium reagents
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The Journal of Organic Chemistry, Vol. 42, Issue 5
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Title: Addition of CFCl3 to Aromatic Aldehydes via in Situ Grignard Reaction

Abstract

Citation Formats

Amorphous Aluminum Bromide Fluoride (ABF) journal, December 2004

Fluorochloro-, fluorobromo-, and monofluorocarbene generation via organolithium reagents journal, March 1977

Addition of CFCl3to Aromatic Aldehydes under Ultrasonic Irradiation journal, January 2006

Addition of CFCl3 to Aromatic Aldehydes under Ultrasonic Irradiation. journal, July 2006

New Synthetic Routes Towards Various α-Fluorinated Aryl Ketones and Their Enantioselective Reductions Using Baker′s Yeast. journal, May 2007

Chemistry of Trichlorofluoromethane: Synthesis of Chlorofluoromethyl Phenyl Sulfone and Fluoromethyl Phenyl Sulfone and Some of Their Reactions journal, January 2001

A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides journal, June 2004

Chlorofluorocarbene from reaction of fluorotrichloromethane with reduced titanium. Synthesis of 1-chloro-1-fluorocyclopropanes journal, January 1990

Interconversion of chlorofluorocarbons in plasmas journal, January 1995

Interconversion of chlorofluorocarbons in plasmas journal, January 1995

Hydrophobic Vitamin B12. Part 20: Supernucleophilicity of Co(I) Heptamethyl Cobyrinate toward Various Organic Halides journal, May 2005

Amorphous Aluminum Bromide Fluoride (ABF) journal, December 2004

A Novel Approach to 2-Chloro-2-fluorostyrenes journal, January 2003

Chemistry of Trichlorofluoromethane: Synthesis of Chlorofluoromethyl Phenyl Sulfone and Fluoromethyl Phenyl Sulfone and Some of Their Reactions journal, January 2001

Reductive alkylation of perfluorocarboxylic acid esters with CCl3F or CCl4 and synthesis of higher linear perfluoroketones journal, December 2004

Addition of CFCl3 to Aromatic Aldehydes under Ultrasonic Irradiation. journal, July 2006

New synthetic routes towards various α-fluorinated aryl ketones and their enantioselective reductions using baker's yeast journal, January 2007

Reductive addition of polychlorofluoroalkanes to fluorocarbonyl compounds journal, June 1996

Reductive addition of trichlorofluoromethane to ketones initiated by the Mg/LiC1 system journal, April 1994

The Halogen/Magnesium-Exchange Using iPrMgCl·LiCl and Related Exchange Reagents journal, January 2014

A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides journal, June 2004

Highly Enantiomerically Enrichedα-Haloalkyl Grignard Reagents journal, September 2000

A Facile Procedure for the Generation of Dichlorocarbene from the Reaction of Carbon Tetrachloride and Magnesium using Ultrasonic Irradiation journal, July 2003

Chlorofluorocarbene from reaction of fluorotrichloromethane with reduced titanium. Synthesis of 1-chloro-1-fluorocyclopropanes journal, January 1990

A remarkably simple preparation of (trifluoromethyl)cadmium and -zinc reagents directly from difluorodihalomethanes journal, August 1985

Fluorochloro-, fluorobromo-, and monofluorocarbene generation via organolithium reagents journal, March 1977

Direct electroreduction or use of an electrogenerated base : two ways for the coupling of polyhalogenated compounds with aldehydes or ketones. journal, February 1997

1, 1-Diaryl- and 1-Aryl-2-chloro-2-fluoroethylenes journal, May 1967

Title: Addition of CFCl₃ to Aromatic Aldehydes via in Situ Grignard Reaction

Amorphous Aluminum Bromide Fluoride (ABF)
journal, December 2004

Fluorochloro-, fluorobromo-, and monofluorocarbene generation via organolithium reagents
journal, March 1977

Addition of CFCl₃to Aromatic Aldehydes under Ultrasonic Irradiation
journal, January 2006

Addition of CFCl3 to Aromatic Aldehydes under Ultrasonic Irradiation.
journal, July 2006

New Synthetic Routes Towards Various α-Fluorinated Aryl Ketones and Their Enantioselective Reductions Using Baker′s Yeast.
journal, May 2007

Chemistry of Trichlorofluoromethane: Synthesis of Chlorofluoromethyl Phenyl Sulfone and Fluoromethyl Phenyl Sulfone and Some of Their Reactions
journal, January 2001

A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides
journal, June 2004

Chlorofluorocarbene from reaction of fluorotrichloromethane with reduced titanium. Synthesis of 1-chloro-1-fluorocyclopropanes
journal, January 1990

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journal, January 1995

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journal, January 1995

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Reductive alkylation of perfluorocarboxylic acid esters with CCl3F or CCl4 and synthesis of higher linear perfluoroketones
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Addition of CFCl3 to Aromatic Aldehydes under Ultrasonic Irradiation.
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The Halogen/Magnesium-Exchange Using iPrMgCl·LiCl and Related Exchange Reagents
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A LiCl-Mediated Br/Mg Exchange Reaction for the Preparation of Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides
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Highly Enantiomerically Enrichedα-Haloalkyl Grignard Reagents
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A Facile Procedure for the Generation of Dichlorocarbene from the Reaction of Carbon Tetrachloride and Magnesium using Ultrasonic Irradiation
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Chlorofluorocarbene from reaction of fluorotrichloromethane with reduced titanium. Synthesis of 1-chloro-1-fluorocyclopropanes
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