Submission Date

7-21-2025

Document Type

Paper- Restricted to Campus Access

Department

Chemistry

Faculty Mentor

Julianne Yost

Student Contributor

Lucy Cornett

Comments

Presented during the 27th Annual Summer Fellows Symposium, July 18, 2025 at Ursinus College.

This research was supported by Drs. Robert ’77 and Elizabeth ’78 Clemens in honor of Florence Tindall Clemens ’55.

Project Description

Indoles are common nitrogen-containing heterocycles that are found in a variety of biologically active compounds and pharmaceuticals. They are privileged scaffolds, serving as core templates to construct functionalized molecules essential for drug discovery. A common reaction used to substitute heterocycles by forming new carbon–carbon bonds is the palladium-catalyzed Suzuki cross-coupling reaction. However, standard reaction conditions typically involve protocols that are detrimental to the environment involving high palladium catalyst loadings, high reaction temperatures, and eco-unfriendly solvents. In recent years, there has been growing interest in finding greener reaction conditions for Suzuki cross-couplings. This work focused on applying our previously developed Suzuki method to unprotected indoles and optimizing the conditions to be more environmentally friendly. To find the best set of conditions for our system, palladium catalyst, base, and solvent were initially screened. Time and temperature were also reduced to make the reaction more sustainable. After screening several variables, we were able to identify greener reaction conditions. These optimized conditions will be used next to examine substrate scope. Having an eco-friendlier method is a definite advantage for the application of this reaction to drug discovery and industrial-scale processes.

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