Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

27 September 2018, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

Keywords

C-H Activation
Carbon Dioxide
Green Chemistry
Amines

Supplementary materials

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Title
ChemRxiv - CO2 mediated CH Arylation of benzylamines - SI - Final
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