Superelectrophilic Fe(III)-Ion Pairs as Stronger Lewis Acid Catalysts for ()-Selective Intermolecular Carbonyl-Olefin Metathesis.

Org Lett

Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Published: April 2020

AI Article Synopsis

Article Abstract

An intermolecular carbonyl-olefin metathesis reaction is described that relies on superelectrophilic Fe(III)-based ion pairs as stronger Lewis acid catalysts. This new catalytic system enables selective access to ()-olefins as carbonyl-olefin metathesis products. Mechanistic investigations suggest the regioselective formation and stereospecific fragmentation of intermediate oxetanes to be the origin of this selectivity. The optimized conditions are general for a variety of aryl aldehydes and trisubstituted olefins and are demonstrated for 28 examples in up to 64% overall yield.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.0c00917DOI Listing

Publication Analysis

Top Keywords

carbonyl-olefin metathesis
12
pairs stronger
8
stronger lewis
8
lewis acid
8
acid catalysts
8
intermolecular carbonyl-olefin
8
superelectrophilic feiii-ion
4
feiii-ion pairs
4
catalysts -selective
4
-selective intermolecular
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!