Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 18, Pages 13025-13040Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01764
Keywords
-
Categories
Funding
- Edward and Virginia Taylor Fund
- Organic Syntheses Inc.
Ask authors/readers for more resources
In this report, a general synthetic approach to bench-stable N-quaternized ketene N,O-acetals was described. These compounds can be used as reagents or synthetic intermediates in multiple reaction types, showing a broad potential in organic synthesis.
N-Quaternized ketene N,O-acetals are typically an unstable, transient class of compounds most commonly observed as reactive intermediates. In this report, we describe a general synthetic approach to a variety of bench-stable N-quaternized ketene N,O-acetals via treatment of pyridine or aniline bases with acetylenic ethers and an appropriate Bronsted or Lewis acid (triflic acid, triflimide, or scandium(III) triflate). The resulting pyridinium and anilinium salts can be used as reagents or synthetic intermediates in multiple reaction types. For example, N-(1-ethoxyvinyl)pyridinium or anilinium salts can thermally release highly reactive O-ethyl ketenium ions for use in acid catalyst-free electrophilic aromatic substitutions. N-(1-Ethoxyvinyl)-2-halopyridinium salts can be employed in peptide couplings as a derivative of Mukaiyama reagents or react with amines in nucleophilic aromatic substitutions under mild conditions. These preliminary reactions illustrate the broad potential of these currently understudied compounds in organic synthesis.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available