Work

Carbon Dioxide-Mediated C( sp 2 )–H Arylation of Primary and Secondary Benzylamines

Year: 2019

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.9b03375

Authors: Mohit Kapoor, Pratibha Chand-Thakuri, Michael C. Young

Institution: University of Toledo

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Herman Frasch Foundation for Chemical Research, University of Toledo

Award: G8021022995