Unconventional Site Selectivity in Cross-Couplings of Dihaloheteroarenes

Unconventional Site Selectivity in Cross-Couplings of Dihaloheteroarenes

Apr 28, 2023 - 1:10 PM
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Headshot of speaker

Dr. Sharon Neufeldt, Montana State University

Host: Dr. Li

Heteroarenes are ubiquitous motifs in high-value small molecules including pharmaceutical drugs and agrichemicals. Elaboration of halogenated heteroaromatic cores can be achieved through cross-coupling reactions, which are among the most widely used methods in organic synthesis. However, when two or more halides are present on the substrate, controlling site selectivity becomes critical. In fact, cross-couplings often follow a predictable selectivity pattern. For many dihalogenated heteroarenes, methods do not exist to reliably invert the conventional pattern to achieve cross-coupling at the "less reactive" C—X bond. Herein we describe new catalyst-controlled strategies to accomplish this goal, together with mechanistic studies to explain the origin of the selectivity inversion.

Sharon R. Neufeldt grew up in Tucson, AZ, earned a B.S. in Chemistry from Northern Arizona University in Flagstaff, and a Ph.D. from the University of Michigan in Ann Arbor. At Michigan, she worked with Professor Melanie Sanford on the development of Pd-catalyzed C—H functionalization reactions. In 2013, she became the Cram Teacher-Scholar at UCLA. There, she undertook postdoctoral research with Professor K. N. Houk using DFT to study the mechanism and selectivity of transition metal-catalyzed C—H activation, while also teaching sophomore organic chemistry. In summer 2016 she moved to Bozeman, MT as an Assistant Professor of Chemistry. She is the recipient of an NSF CAREER award (2019), a Thieme Chemistry Journals Award (2020), a Cottrell Scholars Award (2020), and an NIH NIGMS MIRA award (2020).