Borylation of Thioethers

Description/Abstract/Artist Statement

Late-stage functionalization of natural products and pharmaceuticals use CH functionalization to diversify the complex motif late in the synthesis accessing a large number of complex derivatives in a single step. Within CH functionalization, CH borylation is actively investigated due to the use of boronic acids and boronic esters in Suzuki coupling. Within the pharmaceutical industry, Suzuki coupling is one of the most frequently used transformations. However, regioselectivity of the CH borylation reaction remains a challenge to the field. Organosulfur molecules have a prominent role in drug therapies. More specifically, thioethers and other sulfur moieties make up a quarter of small-molecule pharmaceuticals. However, there is a lack of information about thioethers and the selectivity of CH borylations with these compounds. This project aims to synthesize thioethers and investigate their selectivity towards CH borylation as well as develop a regioselective CH borylation using the thioethers.

Presenting Author Name/s

Stephonda Lewis

Faculty Advisor/Mentor

Dr. Kyle Lambert

Faculty Advisor/Mentor Department

Chemistry Department

College Affiliation

College of Sciences

Presentation Type

Oral Presentation

Disciplines

Organic Chemistry

Session Title

College of Sciences Presentations

Location

Learning Commons @Perry Library, Room 1310

Start Date

3-25-2023 12:00 PM

End Date

3-25-2023 1:00 AM

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Mar 25th, 12:00 PM Mar 25th, 1:00 AM

Borylation of Thioethers

Learning Commons @Perry Library, Room 1310

Late-stage functionalization of natural products and pharmaceuticals use CH functionalization to diversify the complex motif late in the synthesis accessing a large number of complex derivatives in a single step. Within CH functionalization, CH borylation is actively investigated due to the use of boronic acids and boronic esters in Suzuki coupling. Within the pharmaceutical industry, Suzuki coupling is one of the most frequently used transformations. However, regioselectivity of the CH borylation reaction remains a challenge to the field. Organosulfur molecules have a prominent role in drug therapies. More specifically, thioethers and other sulfur moieties make up a quarter of small-molecule pharmaceuticals. However, there is a lack of information about thioethers and the selectivity of CH borylations with these compounds. This project aims to synthesize thioethers and investigate their selectivity towards CH borylation as well as develop a regioselective CH borylation using the thioethers.