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

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...

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Veröffentlicht in:Organic letters 2016-11, Vol.18 (21), p.5620-5623
Hauptverfasser: Reddy, M. Damoder, Fronczek, Frank R, Watkins, E. Blake
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02848