C-H bond functionalization offers considerable benefits in efficiency and economy. Impressive levels of regioselectivity have also been achieved by combining C-H functionalization with directing groups. However, direct arene meta NH2 amination has been elusive. In this presentation, we report a high level of meta-selective NH2 amination of benzyl picolates and related esters via FeCl3-catalysis using commercial hydroxylamine-O-sulfonic acid (HOSA) at rt. Picolate esters are easily prepared/removed for operational simplicity and all of the reaction reagents are inexpensive. Mechanistic insights, scope, and applications to late-stage examples will be presented.

Directed meta C-H amination of benzyl picolates via FeCl3-catalysis

2019 Fall National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.