Submission Date

7-21-2025

Document Type

Paper- Restricted to Campus Access

Department

Chemistry

Faculty Mentor

Julianne Yost

Student Contributor

Tyler J. Moyer

Comments

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

Project Description

Indoles are nitrogen-containing heterocycles widely distributed in natural products and are one of the most important structural scaffolds for the design of new pharmaceuticals from antibiotics to anti-cancer drugs. However, the chemical reactivity of unprotected indoles can lead to side reactions, posing a definite synthetic challenge. For instance, many of the standard protocols for palladium-catalyzed cross-coupling reactions fail in the presence of substrates bearing free NH groups. We previously performed Suzuki- Miyaura cross-coupling reactions, although the indole NH group was always protected, adding an onerous extra step to our synthetic route. The goal of this study was to explore the use of different catalysts, bases, and solvents to perform Suzuki cross-coupling reactions on unprotected indoles—in a more efficient and green manner. Catalyst loading, temperature, and reaction time were also reduced allowing for milder conditions. With optimized reaction conditions in hand, next steps include exploring substrate scope to assess the applicability to a wide range of derivatives.

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