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College of the Sciences

Timothy Beng publishes paper in Journal of Organic and Biomolecular Chemistry

Paper Title: Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C-H activation/cross-coupling of cyclic enamides with boronic acidsCitation: Org. Biomol. Chem., 2016, Advance Article, DOI: 10.1039/C5OB02263K

Authors: Timothy K. Beng, Spencer Langevin, Hannah Braunstein and Monique Khim

In this embodiment, the α-regioselective cross-coupling of cyclic enamides with aryl and alkenyl boronic acids, under ruthenium catalysis, on three privileged drug scaffolds (i.e., the piperidine, pyrrolidine, and azepane heterocycles) is described. The highlights of these studies are the ability to utilize a commercially available ruthenium pre-catalyst in a carbonyl-assisted, chelation controlled mechanism and selectively activate an α-amino sp2 C-H bond in the presence of a β-amino sp2 C-H and an α-amino sp3 C-H bond. The ability to install diverse functionality, using a cheap nontoxic metal such as ruthenium, and the excellent regiocontrol are some of the practical and conceptual merits offered by the current strategy over existing tactics.
The authors are confident that the synthesis and medicinal chemistry communities will embrace these findings since they offer direct access to functionalized piperidine, pyrrolidine and azepane derivatives via carbonyl-assisted C-H activation.

The authors are grateful to Central Washington University for financial support through the donation of startup funds to T.KB. Professors Levente Fabry, JoAnn Peters, Gil Belofsky, and Blaise Dondji are thanked for initial assistance with logistics. Brian Finn and Jeff Wilcox are greatly acknowledged for NMR assistance.

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