Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines

24 September 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The manuscript describes a Pd-catalyzed reaction of benzylic electrophiles that gives para-substituted arene products. Mechanistic studies suggest a mechanism involving a dearomative C–C bond-forming step, followed by base-mediated rearomatization. This mechanism is uncommon and underappreciated in Pd-catalysis and further exploitation of this mechanism should enable access to other organic molecules.

Keywords

palladium
dearomatization
para-selective functionalization
amine bases

Supplementary materials

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SI 1 Experimental C-H functionalization
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SI 2 NMR Spectra
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SI 3 Computational C-H Functionalization
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