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 acids

Authors

Timothy K. Beng, Central Washington UniversityFollow
Spencer Langevin, Central Washington University
Hannah Braunstein, Central Washington University
Monique Khim, Central Washington University

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.

Comments

This article was originally published in Organic & Biomolecular Chemistry. The full-text article from the publisher can be found here.

Due to copyright restrictions, this article is not available for free download from ScholarWorks @ CWU.

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