Synthesis of Arylamines via Aminium Radicals.

Angew Chem Int Ed Engl 2017 11 24;56(47):14948-14952. Epub 2017 Oct 24.

School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but still challenging. We demonstrate that protonated electron-poor O-aryl hydroxylamines give aminium radicals in the presence of Ru(bpy) Cl . These highly electrophilic species undergo polarized radical addition to aromatic compounds in high yield and selectivity. We successfully applied this method to the late-stage modification of chiral catalyst templates, therapeutic agents, and natural products.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.201708693DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5698739PMC
November 2017
9 Reads

Publication Analysis

Top Keywords

therapeutic agents
8
aminium radicals
8
desirable challenging
4
blocks desirable
4
yield selectivity
4
high yield
4
demonstrate protonated
4
challenging demonstrate
4
selectivity applied
4
simple building
4
polarized radical
4
construction structural
4
structural motifs
4
motifs simple
4
applied method
4
building blocks
4
electron-poor o-aryl
4
highly electrophilic
4
addition aromatic
4
electrophilic species
4

Altmetric Statistics

Similar Publications