Abstract

2,5-Disubstituted 3-fluorothiophene derivatives are of interest as building blocks in liquid crystal materials synthesis. This poster details the development of 2-thienyl carbamates and related compounds as flexible building blocks for the construction of 2,5-disubstituted 3-fluorothiophenes. Our approach involves oxidation of 5-substituted 2-thienyl trifluoroborates to the corresponding thienones followed by O-trapping of the corresponding enolate as the 2-thienyl carbamate. Studies aimed at the elaboration of to 2,5-disubstituted 3-fluorothiophenes using a sequential directed ortho-metalation/fluorination/Ni-catalyzed cross-coupling approach will be presented.

Modified Abstract

2,5-Disubstituted 3-fluorothiophene derivatives are of interest as building blocks in liquid crystal materials synthesis. This poster details the development of 2-thienyl carbamates and related compounds as flexible building blocks for the construction of 2,5-disubstituted 3-fluorothiophenes. Our approach involves oxidation of 5-substituted 2-thienyl trifluoroborates to the corresponding thienones followed by O-trapping of the corresponding enolate as the 2-thienyl carbamate. Studies aimed at the elaboration of to 2,5-disubstituted 3-fluorothiophenes using a sequential directed ortho-metalation/fluorination/Ni-catalyzed cross-coupling approach will be presented.

Research Category

Physics/Chemisty/Liquid Crystal

Primary Author's Major

Chemistry

Mentor #1 Information

Dr. Paul Sampson

Mentor #2 Information

Dr. Alexander Seed

Presentation Format

Poster

Start Date

March 2016

Research Area

Materials Chemistry | Organic Chemistry

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Mar 15th, 1:00 PM

Studies Towards The Synthesis of 2,5-Disubstituted-3-Flurothiophenes Using a Tandem Directed Ortho Metallation/Nickel Catalyzed Cross-Coupling Approach

2,5-Disubstituted 3-fluorothiophene derivatives are of interest as building blocks in liquid crystal materials synthesis. This poster details the development of 2-thienyl carbamates and related compounds as flexible building blocks for the construction of 2,5-disubstituted 3-fluorothiophenes. Our approach involves oxidation of 5-substituted 2-thienyl trifluoroborates to the corresponding thienones followed by O-trapping of the corresponding enolate as the 2-thienyl carbamate. Studies aimed at the elaboration of to 2,5-disubstituted 3-fluorothiophenes using a sequential directed ortho-metalation/fluorination/Ni-catalyzed cross-coupling approach will be presented.