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 acids
Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
11-27-2015
Abstract
The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described. The desired outcome is achieved through ruthenium-catalyzed, site-selective sp2 C–H activation/cross-coupling with aryl and alkenyl boronic acids. The regioselectivity (α-sp2vs. α-sp3vs. β-sp2 C–H functionalization) is governed by the rate differences between sp2 and sp3 C–H activation and the necessity for chelation between the ruthenium metal and the carbonyl directing group.
Recommended Citation
Beng, T. K., Langevin, S., Braunstein, H., & Khim, M. (2016). 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 acids. Organic & Biomolecular Chemistry, 14(3), 830–834. https://doi.org/10.1039/c5ob02263k
Journal
Organic & Biomolecular Chemistry
Rights
© The Royal Society of Chemistry 2014
Comments
This article was originally published in Organic & Biomolecular Chemistry. The full-text article from the publisher can be found here.
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