Heterocycles, particularly those containing nitrogen, are present in many biologically relevant and naturally occurring molecules. Specifically, indolines are ubiquitous in vitamins, nucleic acids, antibiotics, hormones, and other essential molecules. Previously reported methodologies to access indolines are limited to intramolecular transformations, and often require expensive, air sensitive starting materials. In addition, these methodologies offer a limited scope. Our recently developed ligand platform demonstrates the efficacy of urea as a palladium ligand to successfully catalyze the heteroannulation of tosylated bromoanilines with 1,3-dienes. Our approach addresses previous shortcomings by using bench stable and relatively cheap bromoanilines. Furthermore, we are able to expand the scope of this chemistry to engage sensitive and sterically demanding substrates while reducing both catalyst and ligand loading as well as equivalents of the π-coupling partner.

Palladium-urea catalyzed heteroannulation of bromoanilines with 1,3-dienes

Fall 2022 abstracts, posters, and presentations will launch in mid-September.

ACS Fall 2022

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