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Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series

Institut Lavoisier de Versailles, UVSQ, CNRS, Université Paris-Saclay, 78035 Versailles, France
Author to whom correspondence should be addressed.
Catalysts 2018, 8(4), 139;
Received: 12 March 2018 / Revised: 26 March 2018 / Accepted: 29 March 2018 / Published: 31 March 2018
(This article belongs to the Special Issue Catalyzed Mizoroki–Heck Reaction or C–H activation)
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5,6-Dihydrobenzo[c]acridine belongs to the large aza-polycyclic compound family. Such molecules are not fully planar due to the presence of a partially hydrogenated ring. This paper describes the first Pd-catalyzed alkoxylation via C-H bond activation of variously substituted 5,6-dihydrobenzo[c]acridines. We determined suitable conditions to promote the selective formation of C-O bonds using 10% Pd(OAc)2, PhI(OAc)2 (2 eq.) and MeOH as the best combination of oxidant and solvent, respectively. Under these conditions, 5,6-dihydrobenzo[c]acridines bearing substituents at both rings A and D were successfully functionalized, giving access to polysubstitutited acridine motifs. View Full-Text
Keywords: C-H activation; palladium; alkoxylation; dihydrobenzo[c]acridine C-H activation; palladium; alkoxylation; dihydrobenzo[c]acridine

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Large, B.; Bourdreux, F.; Damond, A.; Gaucher, A.; Prim, D. Palladium-Catalyzed Regioselective Alkoxylation via C-H Bond Activation in the Dihydrobenzo[c]acridine Series. Catalysts 2018, 8, 139.

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