"Rh-Catalyzed, Regioselective, C-H Bond Functionalization: Access to Qu" by M Damoder Reddy, Frank R. Fronczek et al.

Faculty Publications

Title

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

Authors

M Damoder Reddy, Department of Pharmaceutical Sciences, School of Pharmacy, Union University , 1050 Union University Drive, Jackson, Tennessee 38305, United States.
Frank R. Fronczek, Department of Chemistry, Louisiana State University , 608 Choppin Hall, Baton Rouge, Louisiana 70803, United States.
E Blake Watkins, Department of Pharmaceutical Sciences, School of Pharmacy, Union University , 1050 Union University Drive, Jackson, Tennessee 38305, United States.

Document Type

Article

Publication Date

11-4-2016

Abstract

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(sp)-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.

Publication Source (Journal or Book title)

Organic letters

First Page

5620

Last Page

5623

Recommended Citation

Reddy, M. D., Fronczek, F. R., & Watkins, E. B. (2016). Rh-Catalyzed, Regioselective, C-H Bond Functionalization: Access to Quinoline-Branched Amines and Dimers. Organic letters, 18 (21), 5620-5623. https://doi.org/10.1021/acs.orglett.6b02848

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