Submission Date

5-4-2026

Document Type

Paper- Restricted to Campus Access

Department

Chemistry

Adviser

Julianne M. Yost

Committee Member

Ryan R. Walvoord

Committee Member

Carlita B. Favero

Department Chair

Amanda J. Reig

Project Description

Indoles are common nitrogen-containing heterocycles found in a variety of biologically active compounds and pharmaceuticals. They are considered privileged scaffolds, serving as core templates for the synthesis of more complex molecules essential to drug discovery. A commonly used reaction to modify indoles is the Suzuki–Miyaura cross-coupling reaction. However, standard reaction conditions typically rely on protocols that are detrimental to the environment involving high catalyst loadings, high reaction temperatures, and eco-unfriendly solvents. In recent years, there has been increasing interest in developing greener conditions for Suzuki reactions. This work focused on optimizing our previous Suzuki method to be more environmentally friendly. After systematically screening different catalysts, bases, solvents, and temperatures, greener reaction conditions were identified. Preliminary evaluation of the reaction scope showed wide applicability of these greener conditions with only minor modifications. 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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