Interrupted SAr-Alkylation Dearomatization.

JACS Au

Drexel University, Department of Chemistry, 3041 Chestnut Street, Philadelphia, Pennsylvania 19104, United States.

Published: March 2024

Dearomatizations provide powerful synthetic routes to rapidly assemble substituted carbocycles and heterocycles found in a plethora of bioactive molecules. Harnessing the advantages of dearomatization typically requires vigorous reagents because of the difficulty in disrupting the stable aromatic core. A relatively mild dearomatization strategy is described that employs lithiated nitriles or isocyanides in a simple SAr-type addition to form σ-complexes that are trapped by alkylation. The dearomatizations are diastereoselective and efficient and rapidly install two new carbon-carbon bonds, one of which is a quaternary center, as well as nitrile, isocyanide, and cyclohexadiene functionalities.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10976598PMC
http://dx.doi.org/10.1021/jacsau.3c00813DOI Listing

Publication Analysis

Top Keywords

interrupted sar-alkylation
4
sar-alkylation dearomatization
4
dearomatization dearomatizations
4
dearomatizations provide
4
provide powerful
4
powerful synthetic
4
synthetic routes
4
routes rapidly
4
rapidly assemble
4
assemble substituted
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!