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submitted on 24.01.2020 and posted on 27.01.2020by Vinod Landge, Justin Maxwell, Pratibha Chand-Thakuri, Mohit Kapoor, Evan Diemler, Michael Young
Although C–H activation has become a powerful
tool in the synthesis of complex molecules from simple precursors, transition
metal-catalyzed reactions involving free alkenes often lead to insertion-type
reactions. Herein we demonstrate that the addition of carbon dioxide in the
form of dry ice allows the C(sp2)–H
arylation of both secondary and primary allylamines in the presence of a PdII
catalyst. Notably, the product 3,3’-diarylallylamine motif is prevalent in a
variety of biologically-relevant structures, and this method represents the
most straightforward synthesis of these targets to date. Key features of the
method are the ability to access relatively mild conditions that facilitate a
broad substrate scope, as well as direct diarylation of terminal allylamine
substrates. In addition, several complex and therapeutically-relevant molecules
are included to demonstrate the utility of the transformation.
ACS Herman Frasch Foundation (830-HF17), Start-up from The University of Toledo. ETD thanks The University of Toledo - Office of Undergraduate Research for an USRCAP Fellowship in support of this work.