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Rh-Catalyzed, Regioselective, C–H Bond Functionalization: Access to Quinoline-Branched Amines and Dimers

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† Department of Pharmaceutical Sciences, School of Pharmacy, Union University, 1050 Union University Drive, Jackson, Tennessee 38305, United States
‡ Department of Chemistry, Louisiana State University, 608 Choppin Hall, Baton Rouge, Louisiana 70803, United States
*E-mail: [email protected]
Cite this: Org. Lett. 2016, 18, 21, 5620–5623
Publication Date (Web):October 17, 2016
https://doi.org/10.1021/acs.orglett.6b02848
Copyright © 2016 American Chemical Society
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    Abstract

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    Rh-catalyzed, chelation-induced, C-5 regioselective C–H functionalization of 8-amidoquinolines with a range of N-Boc aminals is reported for the first time. The addition of in situ generated imines to C(sp2)–H bonds afforded branched amines in good to excellent yields. Moreover, this transformation features good functional group compatibility, broad substrate scope, and mild reaction conditions and is suitable for gram-scale synthesis. In addition, an unprecedented, chelation-induced, site-selective, remote dimerization of quinolines led to the formation of dimer frameworks in moderate yields under Rh-catalyzed conditions.

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    • General experimental procedures and spectroscopic data of all the compounds; 2D-NMR and HRMS spectral data for representative compounds; and X-ray crystallographic data for 3a (PDF)

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